Condensed palatinose in hydrogenated form

ABSTRACT

The present invention relates to processes for preparing condensed Palatinose in hydrogenated form to hydrogenated condensed Palatinose thus prepared, to uses of the same, and to foodstuffs and drugs comprising hydrogenated condensed Palatinose.

The present invention relates to hydrogenated condensed Palatinose, toprocesses for preparing the same, to uses of the same, and to foodstuffsand drugs comprising hydrogenated condensed Palatinose.

Free radicals are unstable and highly reactive atoms, molecules orresidues having unpaired electrons, and are formed continuously in thebody by biochemical oxidation-reduction reactions in the presence ofoxygen, by phagocytes, contact with environmental toxins, ionizingradiation, UV rays or severe physical strain. Because of their extremereactivity, free radicals represent a potential threat for healthy cellsand their components. Cell components particularly affected areproteins, nucleic acids and polyunsaturated fatty acids in cellmembranes.

The cells are protected from the effects of free radicals principallythrough the antioxidants, which act as radical scavengers. Ifantioxidants are not present in sufficient amount, the protectionpossessed by the cells against free radicals is inadequate. Reducedamounts of antioxidants are observed, for example, in the case ofdiseases such as cancer, diabetes, hypertension, male infertility,rheumatic disorders and chronic inflammatory diseases. Antioxidants alsoplay a large part in detoxification and in the breakdown of xenobioticswith which humankind comes into contact owing to indoor pollution in thedomestic sphere or at the workplace or owing to incorrect diet. Examplesof known primary endogenous antioxidants include superoxide dismutase(SOD), glutathione peroxidase (GPx), glutathione, catalase, ferritin andcoeruloplasmin.

Glutathione (GSH) is a cysteine-containing tripeptide and the mostcommon thiol compound in mammalian cells. GSH is a substrate for theenzymes glutathion S-transferase and GSH peroxidase, which catalyzereactions for the detoxification of xenobiotic compounds and for theoxidation inhibition of reactive oxygen molecules and free radicals. Asthe substrate of glutathione S-transferase, glutathione is converted byreversible oxidation into the corresponding disulfide GSSG. Glutathionethereby constitutes a buffer system for the redox state of the cell.Glutathione is additionally involved in cysteine transport, inleukotriene and prostaglandin metabolism, in deoxyribonucleotidesynthesis, in immune functions and in cell proliferation (Bray andTaylor, Canadian J. Physiol. Pharmacol., 71 (1995) 746-51). Theimportance of glutathione particularly for the intestinal tract isevident from the massive damage to the intestinal mucosa that isobserved in the case of GSH deficiency, as for example followingtreatment with the GSH-synthesis inhibitor buthionine sulfoximine(Martensson et al., Proc. Natl. Acad. Sci. USA, 87 (1990), 1715-19). Thetissue concentration of GSH is regulated by a variety of factors, whichinclude the nutritional state and the food itself. Between tissue GSHconcentration, nutrition and oxidative stress, therefore, there is aclose relationship.

Glutathione S-transferases (GSTs) form one of the most importantdetoxification systems of the cells, particularly during phase II ofcell division. Detoxification is accomplished by transfer of glutathioneto electrophilic components which are formed, for example, during themetabolism of carcinogens. The GST-catalyzed nucleophilic attack ofglutathione on electrophilic substrates greatly lessens their reactivitywith respect to cellular macromolecules. GSTs are able in this waygreatly to lessen the activity of a range of chemical carcinogens. GSTstherefore play an important physiological part in protection againstoxidative stress and associated disorders, especially cancer illnesses.All eukaryotes possess a number of cytosolic and membrane-boundglutathione S-transferases (Hayes and Pulford, Critical Reviews inBiochemistry and Molecular Biology, 30 (1995) 445-600). The expressionof GST is tissue-specific. Glutathione S-transferases of the α class areexpressed, for example, in the liver, kidneys and testes but not in thelung. In the intestine, GST forms of the π class are expressed.

The soluble GSTs are dimeric proteins. Each subunit features an activecenter composed of two functional regions, namely a hydrophilic Gdomain, which binds the glutathione substrate, and an adjacent,hydrophobic H domain, to which the various electrophilic substrates bind(Armstrong, Chem. Res. Toxicol., 10 (1997), 2-18). The GSTs catalyzevarious types of reactions, examples being the opening of epoxide rings,nucleophilic aromatic substitution reactions, reversible Michaeladditions to α,β-unsaturated aldehydes and ketones, isomerizations, andsome peroxidase reactions. Known GST substrates include numerous classesof chemical substance, examples being antibiotics, pesticides,insecticides, carcinogens, and medicinal products.

Compounds such as polycyclic aromatic hydrocarbons, phenol antioxidants,reactive oxygen molecules, isothiocyanates, trivalent arsenic compounds,barbiturates, and synthetic glucocorticoids are able to induce GSTactivities, in which case genes which encode the GST enzymes areactivated (Hayes and Pulford, 1995). GST induction takes placeprincipally by way of various transcription mechanisms. The regulationregions of GST-encoding genes contain elements to which theaforementioned substances bind and which are able to induce genetranscription. Known elements are, for example, the glucocorticoid,xenobiotic, and antioxidant response elements (ARE) (Eaton and Bammler,Toxicological Sciences, 49 (1999), 156-64).

Food constituents as well, examples being phytochemical substances, caninduce GST activities, in which case GST forms of the π class in theintestinal region, in particular, are induced. GST induction in theintestinal tract by food constituents is being discussed as a mechanismfor preventing intestinal cancer illnesses (Peters and Roelofs, CancerRes., 52 (1992), 1886-90). Very strong inductors of GSTs areisothiocyanates, which are produced as metabolism products fromglucosinolates, which are found in vegetable species belonging to theCruciferae, such as broccoli, lettuce and brussels sprouts (Vos et al.,Biochem. Pharmacol., 37 (6) (1987), 1077). Glycans act either directlyor indirectly; that is, only after metabolism by the microflora locatedin the intestine.

Of particular importance for GST induction are food constituents whichare indigestible or difficult to digest, in other words dietary fiber,which is resistant to digestion by human enzymes. This includes somecarbohydrates, such as pectin, guar gum and resistant starch, which arefermented only in the intestinal tract by the bacterial flora of thelarge intestine, to form short-chain fatty acids (SCFAs), especiallyacetic acid, propionic acid and butyric acid (Bartram et al., CancerRes., 53 (1993), 3283-88). An investigation by Treptow-van Listhaut etal. (Eur. J. Nutr., 38 (1999), 76-83) showed that rats fed with aretrograded, amylase-resistant starch had higher GST levels than ratsfed with degradable starch, there being a particular increase in thelevels of GST in the intestine. Stein et al. (Eur. J. Clin. Invest., 26(1996), 84-87) showed that the activities of the SCFAs, particularlybutyric acid (butyrate), included inducing the formation of glutathioneS-transferases π, exerting antiproliferative effects on the human largeintestine cancer cell line Caco-2, and increasing differentiation of thecells. The effects observed in the investigation are of physiologicalrelevance insofar as the short-chain fatty acid concentrations used werebelow those normally encountered in the lumen of the large intestine.Moreover, butyrate has an antineoplastic effect, leads to a reduction inpH, improves intestinal function, and may prevent inflammation (Hickman,Clin. Tech. Small Animal Pract., 13 (1998), 211-16).

The fraction of dietary fiber in the food depends on numerous factors,examples including the nature of the foodstuff and the manner of itspreparation. The majority of foods are low in fiber. Vegetables, certaintypes of fruit, nuts, seeds, and, above all, unrefined cereal products,in contrast, are rich in fiber. The significance of the preparation ofthe food for its fiber content is evident from the example of resistantstarch. This is the part of the starch that is not digested in the smallintestine and so passes unchanged into the large intestine. Thus starchfrom freshly boiled potatoes is broken down very effectively in thegastrointestinal tract, with only about 3% of the starch consumedpassing the small intestine unchanged and passing into the largeintestine. If, on the other hand, the potatoes are cooled after boiling,their fraction of resistant starch goes up by a factor of from two tofour. Repeated heating and subsequent cooling intensifies the effect.

One way to compensate for the fiber deficiencies caused by foodstuffsprocessing or for a low-fiber diet and to prevent cancer illnesses viathe food supply is to enrich foodstuffs with dietary fibers or withsubstances which, in a similar way to dietary fibers, pass the smallintestine virtually unchanged and are fermented only in the largeintestine by the intestinal flora. Many of the forms of fiber used todate to enrich foodstuffs, however, have a range of criticaldisadvantages and/or do not fulfill the expectations vested in them withrespect to the prevention of cancer illnesses, particularly of the largeintestine region.

In two long-term studies by the U.S. National Cancer Institute and theUniversity of Arizona it was found that several years of nutrition withhigh-fiber food, with muesli products, for example, apparently had noeffect on the frequency of cancer of the large intestine(http://www.just-another-site.de/, Apr. 20, 2000). The “Nurse Health”study as well showed that, among the 90 000 nurses participating in thestudy, the amount of fiber consumed had no effect on the colonic cancerrisk (Schweinsberg, Int. Conference on Dietary Factors, ERNO 2 (1)(2001), 72-73). These studies, however, included only fiber substancesthat are not fermented in the large intestine region by the intestinalflora.

Wheat bran is frequently used as an addition to low-fiber food. Asinvestigations on rats with respect to the incidence of tumors in thecolon showed, wheat bran diets are hardly suitable for preventingcancer. Wheat bran, much like cellulose, is hardly fermented by colonicbacteria. In the case of foodstuffs enriched with wheat bran, moreover,unwanted side effects occur, such as meteorism and cramplike pains(http://www.pharmazeutische-zeitung.de). It was also found that thephytic acid, which occurs in wheat bran and is a widespread storagesubstance in cereals, legumes and oil seeds, considerably impairsmineral metabolism and prevents the uptake of calcium, magnesium, iron,and zinc. Just 25 g of wheat bran reduce the absorption of calciumconsiderably (Knox et al., Am. J. Clin. Nutr., 53 (1991), 1480-92). Inolder persons and those at increased risk of osteoporosis, therefore, afood enriched with wheat bran is not unproblematic.

Even the resistant starch which can be fermented in principle has aseries of disadvantages. Thus it has turned out that commerciallycustomary resistant starch is in some cases not fermentable, a factwhich is obviously related to the production processes. Only resistantstarch produced using special extrusion processes is butyrogenic, i.e.,leads to the formation of butyric acid. Resistant starch produced underpolymer-protective extrusion conditions, however, is frequently notstable (http://www.igv-gmbh.de/e/tagung/geb-hardt.htm).

The technical problem on which the present invention is based is toprovide agents which are suitable for preventing cancer illnesses,especially cancer of the large intestine, and which do not have thedisadvantages of the prior art forms of fiber, and processes forpreparing them, the agents being easier and less expensive to preparethan the agents used conventionally, and being able to be used as a formof fiber.

The present invention solves this technical problem through theprovision of a process for preparing hydrogenated condensed Palatinoseand also through the provision of the hydrogenated condensed Palatinosethus prepared. The process of the invention for preparing hydrogenatedcondensed Palatinose comprises the catalytic hydrogenation of a solutioncomprising condensed Palatinose and if appropriate the separation of thehydrogenated condensed Palatinose with a degree of polymerization (DP)of 4 to 10 from the reaction mixture. The hydrogenated condensedPalatinose of the invention that is prepared in this way is a mixture inparticular of hydrogenated Palatinose dimers, Palatinose trimers andPalatinose tetramers with a degree of polymerization of 4 to 10.

The hydrogenated condensed Palatinose provided in accordance with theinvention is not cleaved to any notable extent either under the pHconditions of the stomach or by the enzymes of the small intestinemucosa. The hydrogenated condensed Palatinose of the invention is,surprisingly, fermented only by microorganisms in human feces, to formshort-chain fatty acids having a high fraction of butyric acid, aconsiderably greater amount of butyric acid being formed in comparisonto other forms of fermentable fiber such as resistant starch.

Since the hydrogenated condensed Palatinose of the invention, whenconsumed, passes virtually unchanged into the cecum and into the largeintestine, and is only there fermented by the human intestinal flora, itis outstandingly suitable as a form of fiber. Since the hydrogenatedcondensed Palatinose of the invention dissolves readily it isparticularly suitable as a form of soluble fiber which in the largeintestine region, owing to the outstanding solubility, is amenablecompletely, or almost completely, to fermentation. Compared withfrequently used forms of fiber such as wheat bran or oat bran, moreover,the hydrogenated condensed Palatinose of the invention has the advantageof containing no substances which lead to unwanted side effects.

The hydrogenated condensed Palatinose of the invention is also suitableas a highly active agent for preventing and/or treating diseasesassociated with oxidative stress. On the basis of in vitro studies ithas been found that the products of the fermentation of condensedhydrogenated Palatinose, especially butyrate, not only increase theexpression of glutathione S-transferase but also lead to an increasedcellular glutathione concentration. Glutathione and glutathioneS-transferases are involved in the detoxification of electrophilicextraneous substances, whose reactivity with respect to cellularmacromolecules is sharply reduced. Both substances therefore possessimportant detoxification and protective functions with respect to cells,particularly toward the development of tumors. Butyrate, furthermore, isknown to exert an antiproliferative effect on colonic cancer cells. Thehydrogenated condensed Palatinose of the invention, and particularly itsfermentation products, therefore has antioxidative and anticarcinogeniceffects which are substantially reinforced as compared with the effectsof other forms of fiber, particularly condensed Palatinose and resistantstarch, owing to the considerably greater amount of butyric acidproduced during fermentation.

As a consequence of the fermentation of the hydrogenated condensedPalatinose of the invention to form short-chain fatty acids, especiallybutyrate, there is, furthermore, a marked reduction in pH in the largeintestine region, into the acidic range. On the one hand this impairsthe living conditions for pathogenic intestinal microorganisms such asClostridias and on the other hand improves the living conditions foracidophilic microorganisms, examples being the Bifidus flora and lacticacid bacteria. The hydrogenated condensed Palatinose of the inventiontherefore has a prebiotic effect which is substantially reinforcedbecause of the considerably increased production of butyric acid ascompared with condensed Palatinose and resistant starch.

A further feature of the hydrogenated condensed Palatinose of theinvention is that in comparison to other known forms of fiber it is muchbetter able to prevent the development of infectious diseases, since inthe large intestine region on the one hand it suppresses the growth ofpathogenic microbes, owing to the fermentation products that are formed,and, on the other hand, on the basis of its considerably higheravailability, it is able to prevent or reduce the taking up ofpathogenic microbes by human or animal epithelial cells. As a result ofthis the hydrogenated condensed Palatinose of the invention is betterable to strengthen the immune defense and to prevent or control generalinfections and inflammatory diseases, especially chronic intestinalinflammation.

Because of the lower level of degradability in the digestive tract, thehydrogenated condensed Palatinose of the invention is a particularlyeffective modulator of the glycemic properties of foodstuffs of allkinds.

The hydrogenated condensed Palatinose of the invention can be prepared,moreover, very easily and inexpensively from condensed Palatinose, whichfor its part can be produced inexpensively from Palatinose. Palatinose(6-O-α-D-glucopyranosylfructose) can be prepared industrially fromsucrose in accordance with DE 44 14 185 C1 by simple enzymaticrearrangement using immobilized bacterial cells, of the speciesProtaminobacter rubrum, Erwinia rhapontici and Serratia plymuthica, forexample, or using a sucrose isomerase isolated therefrom.

The hydrogenated condensed Palatinose of the invention is prepared inaccordance with the invention initially, in a first step, bycatalytically hydrogenating a solution comprising condensed Palatinose.

In connection with the invention the term “condensed Palatinose” refersin particular to a mixture of Palatinose and condensation productsthereof. The condensation of substances is a chemical reaction whichproceeds, where appropriate, under catalytic influence and in which atleast two molecules combine to form a larger molecule with the egress ofa simple molecule. The term “condensed Palatinose” therefore embraces inparticular a mixture of uncondensed Palatinose, Palatinose dimers,Palatinose trimers, Palatinose tetramers, Palatinose pentamers andtrisaccharides. The trisaccharides consist of the condensation productof a simple sugar from hydrolyzed Palatinose and of a Palatinosedisaccharide.

From the prior art there are a number of processes known for preparingcondensed Palatinose from Palatinose. By way of example it is possibleto prepare condensed Palatinose from an acidified aqueous solution ofPalatinose by heat treatment at temperatures between 100° C. and 170° C.The water content of the initial mixture of water, organic acid andPalatinose in this case is usually about 33%, based on the Palatinoseemployed. In DE 38 18 884 A1 this process is used to give condensedPalatinose having the following composition: about 54% uncondensedPalatinose, about 29.8% Palatinose dimers, about 11.5% Palatinosetrimers, and about 5% Palatinose tetramers. In a process of the samekind an aqueous Palatinose solution containing citric acid is used togive condensed Palatinose with a composition of about 52.4% uncondensedPalatinose, about 26% Palatinose dimers, about 12% Palatinose trimersand about 5.7% Palatinose tetramers (Mutsuo et al., J. Carbohydr. Chem.,12 (1993), 49-61). Likewise known is a process for preparing condensedPalatinose from Palatinose in which Palatinose is reacted with anhydroushydrofluoric acid (HF) to form a mixture composed essentially ofdifferent Palatinose dimers. In the case of this process the reactiontakes place in an anhydrous medium at preferably 0 to 20° C. Thecondensed Palatinose obtained in this process includes about 94%Palatinose dimers and about 2% uncondensed Palatinose (FR 2 680 789 A1).In a further publication the aforementioned anhydrous condensation bymeans of HF gives condensed Palatinose having a Palatinose dimer contentof more than 73% (Defaye et al., Carbohydrate Research, 251 (1994),1-15).

In one preferred embodiment of the invention it is envisaged that thecondensed Palatinose to be hydrogenated is produced by heat-treating anaqueous Palatinose solution having a pH of 3.2 to 5.8 at a temperatureof 100° C. to 170° C. under atmospheric pressure or reduced pressure. Inthis case the aqueous solution of the Palatinose to be condensed isprepared by dissolving Palatinose in water, in particular at atemperature of 105° C. In accordance with the invention it is envisagedthat acidic catalysts are added to the aqueous Palatinose solution.Advantageously the acidic catalysts are H⁺-loaded, strongly acidiccation exchangers, organic acids, boric acid, a combination ofphosphoric acid with potassium dihydrogen phosphate or ammonium sulfate.The organic acids are preferably selected from the group consisting ofcitric acid, malic acid, succinic acid, and tartaric acid.

In one particularly advantageous embodiment of the invention thecondensed Palatinose to be hydrogenated is obtained by heat-treating anaqueous Palatinose solution in the presence of 0.02% by weight of citricacid, based on Palatinose, in vacuo at a temperature of 135° C. Thecondensed Palatinose thus prepared preferably comprises a mixturecomprising about 48% uncondensed Palatinose, about 28% Palatinosedimers, about 12% Palatinose trimers, about 5% Palatinose tetramers,about 5% Palatinose pentamers, and about 2% hydrolysis products.

In a further preferred embodiment of the invention it is envisaged thatthe condensed Palatinose to be hydrogenated is obtained by reaction withanhydrous hydrofluoric acid at a temperature of 0° C. to 20° C. Thereaction mixture obtained in this case preferably comprises about 73% to94% Palatinose dimers.

In another, particularly preferred embodiment of the invention thecondensed Palatinose to be hydrogenated is prepared from a Palatinosemelt. The Palatinose melt is obtained by adding Palatinose to a solutionof a catalytically active, acidic substance in water and heating themixture at a temperature of 130° C. to 160° C. The mixture ofPalatinose, acidic substance, and water used for preparing the melt ischaracterized in that the water fraction is well below 12% by weight. Inaccordance with the invention it is envisaged in particular that thePalatinose mixture comprises 4% to 12% by weight water and 0.05% to 0.5%by weight the acidic substance. The acidic substance can be anH⁺-loaded, strongly acidic cation exchanger, an organic acid, boricacid, a combination of phosphoric acid with potassium dihydrogenphosphate or ammonium sulfate. Preferably the organic acid is an organicacid of low volatility, and more preferably is citric acid.

In one preferred embodiment of the aforementioned process the solutionof the organic acid is heated in water, before and/or during theaddition of the Palatinose, to a temperature of 55° C. to 95° C., morepreferably to about 75° C. The addition of Palatinose to the solution ofthe organic acid in water takes place preferably with stirring. Themixture of Palatinose, organic acid, and water that is used forpreparing the Palatinose melt is then heated to a reaction temperatureof 140° C. to 155° C., more preferably about 145° C., until the meltstage is reached, and the mixture is stirred continuously. The condensedPalatinose is obtained from the melt after about 20 to 100 minutes,preferably after 30 to 60 minutes, the temperature of the melt beingheld in this period at 130° C. to 160° C., preferably at 140° C. to 155°C., more preferably at 145° C.

In another preferred embodiment of the aforementioned process the meltthus obtained, after the reaction has run its course, is slaked withwater, giving a syrup which comprises the condensed Palatinose. Thewater used for slaking the melt is preferably added in a melt/waterweight ratio of 10:1 to 1:2, more preferably 5:1 to 1:1. The condensedPalatinose obtained from the Palatinose melt preferably comprises about15% to 45% by weight uncondensed Palatinose, 35% to 60% by weightPalatinose dimers, less than 10% by weight Palatinose trimers, and lessthan 5% by weight Palatinose tetramers and Palatinose pentamers.

In one preferred embodiment of the present invention the condensedPalatinose obtained by one of the processes described above is depletedprior to catalytic hydrogenation in an additional process step in termsof its uncondensed Palatinose content. The depletion of the condensedPalatinose with respect to uncondensed Palatinose takes place preferablyby means of chromatographic separation of the uncondensed Palatinosefrom the condensed Palatinose obtained. In one preferred version of thisembodiment a cation exchanger loaded in particular with calcium ions isused for the chromatographic separation process. The aforementionedseparation and depletion process gives a condensed Palatinose which ascompared with condensed Palatinose obtained directly from an aqueousPalatinose solution advantageously has a Palatinose dimer (DP=4) contentincreased by about 100% and an uncondensed Palatinose (DP=2) contentreduced by about 75%.

In accordance with the invention it is envisaged that the condensedPalatinose obtained above is converted into an aqueous solution and thensubjected to a catalytic hydrogenation, the catalytic hydrogenation ofthe solution comprising condensed Palatinose taking place, in accordancewith the invention, at elevated temperature under increased pressure inthe presence of hydrogen and using a catalyst.

In connection with the present invention a “hydrogenation” is theintroduction, normally taking place under catalysis, of hydrogen into anorganic compound, in other words a reduction of said compound. Acharacteristic feature of the reduction or hydrogenation process is thatthe compound to be reduced accepts electrons. The “hydrogenation ofcondensed Palatinose” in connection with the present invention means areduction of the anomeric center of unsubstituted fructose. By a“catalytic hydrogenation” is meant a hydrogenation in the presence of acatalyst, i.e., of a substance which lowers the activation energy forthe hydrogenation to take place and thereby raises the reaction rate ofthe hydrogenation without appearing in the end product of thehydrogenation reaction.

In accordance with the invention the solution of the condensedPalatinose to be hydrogenated is prepared by dissolving condensedPalatinose in an aqueous medium, preferably in water, in a concentrationof 20% to 40% by weight, preferably 30% by weight. In accordance withthe invention it is envisaged that the pH of the aqueous solution isadjusted to a value of 6 to 8 using suitable agents. In one preferredembodiment of the invention the pH of the solution of the condensedPalatinose to be hydrogenated is adjusted to 7.8 by adding aqueoussodium hydroxide solution.

In accordance with the invention it is envisaged that the hydrogenationof the solution comprising condensed Palatinose takes place at atemperature of 40° C. to 140° C., in particular 60° C. to 80° C.,preferably 70° C. In accordance with the invention the catalytichydrogenation of the solution comprising condensed Palatinose takesplace in the presence of hydrogen, and in one preferred embodiment ofthe process of the invention it is envisaged that the hydrogen used hasa pressure of 150 to 230 bar, in particular 100 to 200 bar, preferably150 bar.

In accordance with the invention the hydrogenation of the solutioncomprising condensed Palatinose takes place using a catalyst. In onepreferred embodiment of the invention a mixture of a pure Raney metaland of a Raney metal alloy is used as catalyst, the Raney metal beingpreferably nickel, copper, cobalt or iron. The Raney metal alloy ispreferably an alloy of nickel, copper, cobalt or iron with aluminum, tinor silicon. In a further preferred embodiment of the invention thecatalyst used for the hydrogenation comprises as active component one ormore metals of transition group VIII of the periodic table on a support.The active component used is preferably platinum, ruthenium, palladiumand/or rhodium. The catalyst support comprises preferably activatedcarbon, aluminum oxide, zirconium oxide and/or titanium dioxide.

The solution comprising condensed Palatinose is preferably stirredcontinuously during the hydrogenation. In accordance with the inventionit is envisaged in particular that the hydrogenation takes place over aperiod of at least 2 hours to 5 hours, preferably at least four hours.

In accordance with the invention it is envisaged that the hydrogenationof the condensed Palatinose is carried out continuously, semibatchwiseor batchwise. The hydrogenation of the invention can be carried outeither in a fixed-bed process or in a suspension process.

After the condensed Palatinose has been hydrogenated a product mixtureis obtained, in accordance with the invention, that comprises 25% to 36%by weight hydrogenated condensed Palatinose having a DP of 4, 9% to 15%by weight hydrogenated condensed Palatinose having a DP of 6, 3% to 7%by weight hydrogenated condensed Palatinose having a DP of 8, 3% to 7%by weight hydrogenated condensed Palatinose having a DP of 10, 3% to 7%by weight unhydrogenated condensed Palatinose and 40% to 55% by weighthydrogenated uncondensed Palatinose.

In one preferred embodiment of the invention it is envisaged that thehydrogenated condensed Palatinose products having a DP of 4 to 10 thatare obtained after the condensed Palatinose has been hydrogenated areseparated from the reaction mixture and isolated. In accordance with theinvention the separation and isolation of these reaction products can becarried out using any desired physical and/or chemical separationprocesses, which allow the separation of reaction products having adesired degree of polymerization.

For separating the hydrogenated condensed Palatinose products having aDP of 4 to 10 it is preferred to use chromatographic processes. Inconnection with the present invention “chromatographic processes” areany physical processes in which substances are separated by partitionbetween a stationary phase and a mobile phase, the underlying separationmechanisms possibly including adsorption isotherms, distributionisotherms, reversed-phase matrices, ion pair systems, ion exchange, ionexclusion and gel permeation.

In one preferred embodiment of the invention the separation of thehydrogenated condensed reaction products takes place using gelpermeation processes, which are also referred to as exclusionchromatography, molecular sieve chromatography or gel filtrationprocesses. By “gel permeation” is meant the process in which, as aresult of a sieve effect, the migration of molecules through a gelmatrix having a pore structure results in a partition according tomolecular size. In a particularly preferred embodiment of the inventionthe hydrogenated condensed Palatinose products are separated from thereaction mixture using substances such as polydextrans, polyacrylamide,agarose, etc., as the gel matrix.

In one preferred embodiment of the invention hydrogenated condensedreaction products having a DP of 4 to 10 are separated from the reactionmixture using separating columns containing Fractogel HW40S, the flowrate preferably being 600 ml/hour. The resultant fractions ofhydrogenated condensed Palatinose, following further concentration usingcustomary processes, can be freeze-dried and processed further.

After separation from the reaction mixture the hydrogenated condensedPalatinose contains 30% to 55% by weight hydrogenated condensedPalatinose having a DP of 4, 20% to 30% by weight hydrogenated condensedPalatinose having a DP of 6, 7% to 13% by weight hydrogenated condensedPalatinose having a DP of 8, and 2% to 6% by weight hydrogenatedcondensed Palatinose having a DP of 10.

The present invention further provides hydrogenated condensed Palatinoseobtainable in accordance with one of the processes of the inventiondescribed above. The hydrogenated condensed Palatinose obtained inaccordance with the invention constitutes a mixture of differenthydrogenated condensed Palatinose products and comprises at leasthydrogenated condensed Palatinose having a DP of 4, hydrogenatedcondensed Palatinose having a DP of 6, hydrogenated condensed Palatinosehaving a DP of 8, and hydrogenated condensed Palatinose having a DP of10.

The hydrogenated condensed Palatinose of the invention comprises atleast one compound of the formula (1)

obtainable from α-2→1-linked di-Palatinose, for n=0 (DP 4):

-   O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitol    and-   O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]-D-mannitol;    at least one compound of the formula (2)    obtainable from β-2→1-linked di-Palatinose for n=0 (DP 4):-   O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitol    and-   O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]D-mannitol;    at least one compound of the formula (3)    obtainable from α-2→3-linked di-Palatinose:-   O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitol    and-   O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol;    at least one compound of the formula (4)    obtainable from α-2→4-linked di-Palatinose:-   O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitol    and-   O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol;    at least one compound of the formula (5)    obtainable from β-2→3-linked di-Palatinose:-   O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitol    and-   O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol,    and at least one compound of the formula (6)    obtainable from β-2→4-linked di-Palatinose:-   O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitol    and-   O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol;

Preferably the hydrogenated condensed Palatinose of the invention hasthe following composition: 30% to 55% by weight hydrogenated condensedPalatinose having a DP of 4, 20% to 30% by weight hydrogenated condensedPalatinose having a DP of 6, 7% to 13% by weight hydrogenated condensedPalatinose having a DP of 8, and 2% to 6% by weight hydrogenatedcondensed Palatinose having a DP of 10. The fraction of hydrogenatedcondensed Palatinose having a DP of 4 is preferably 35% to 50% byweight. Preferably the fraction of hydrogenated condensed Palatinosehaving a DP of 6 is 22% to 28% by weight. The fraction of hydrogenatedcondensed Palatinose having a DP of 8 is preferably 8% to 12% by weight.The fraction of hydrogenated condensed Palatinose having a DP of 10 ispreferably 3% to 5% by weight. Preferably the hydrogenated condensedPalatinose of the invention additionally comprises 6% to 12% by weightunhydrogenated condensed Palatinose having a DP of 4.

The hydrogenated condensed Palatinose of the invention may compriseadditional constituents, examples being compounds having a DP of 1, suchas glucose, fructose, sorbitol or mannitol, compounds having a DP of 2,such as isomaltulose or Isomalt, compounds having a DP of 3, such asunspecified trisaccharides, and compounds having a DP of 4, such asdi-Palatinose dianhydrides.

In accordance with the invention it has been shown that the hydrogenatedcondensed Palatinose of the invention is, advantageously, resistant orvirtually resistant to breakdown in the mammalian stomach and/or by theenzymes of the mammalian digestive tract.

By means of in vitro investigations it has been shown that thehydrogenated condensed Palatinose prepared in accordance with theinvention, in HCl solutions having a pH of 2.0, in other words underconditions comparable with those to be encountered in the mammalianstomach, surprisingly, undergoes only limited hydrolysis or none at all.From further in vitro investigations it is apparent that hydrogenatedcondensed Palatinose is not broken down by pancreatic enzymes, includingfor example hydrolases, especially carbohydrate-cleaving enzymes such asα-amylase, which cleave α-1,4-glucans (starch, glycogen) to maltose andmalto-oligosaccharides. Nor do the enzyme complexes situated in themucosa in the small intestine, namely saccharase/isomaltase andglucoamylase/maltase, cleave the hydrogenated condensed Palatinoseproduct of the invention to anything more than a limited extent, if atall. These enzyme complexes normally ensure that the maltose and sucrosedisaccharides, and in part malto-oligosaccharides as well, that reachthe small intestine are cleaved to monosaccharides and as such pass viathe intestinal wall into the bloodstream. The hydrogenated condensedPalatinose of the invention is therefore neither hydrolyzed by the pHconditions of the stomach nor degraded to any notable extent by thehuman or animal enzymes of the digestive tract.

In accordance with the invention it has been demonstrated that thehydrogenated condensed Palatinose of the invention is fermented in vitroby microorganisms of the human feces, i.e., microorganisms of theintestinal flora. Formed in the fermentation supernatant in this caseare short-chain fatty acids, particularly butyric acid, the amount ofshort-chain fatty acids formed, and particularly the amount of butyrateformed, being markedly higher than in the case of other forms offermentable fiber. The amount of butyrate produced in the fermentationof the hydrogenated condensed Palatinose of the invention is muchhigher, for example, than the amount of butyrate obtained when resistantstarch is fermented. These metabolites, formed by the intestinalbacteria, are responsible for the induction of glutathioneS-transferase, an enzyme which is able to afford the cells protectionagainst carcinogens and oxidants.

The induction of glutathione S-transferase by the fermentation productsof the hydrogenated condensed Palatinose of the invention wasdemonstrated in further tests in vitro. The supernatant formed in thefermentation of hydrogenated condensed Palatinose by intestinal bacterialed to a significant increase in glutathione S-transferase activity inthe human colon cell line HT 29. The GST activity induced by thefermentation products of hydrogenated condensed Palatinose is markedlyhigher than in the case of controls without carbohydrate, controls withunhydrogenated condensed Palatinose, and controls with resistant starch.The intracellular glutathione content as well was increasedsignificantly, by 60% compared to controls, by hydrogenated condensedPalatinose. Both glutathione and glutathione S-transferase are known toincrease the protection of the cells with respect to carcinogens andoxidants.

In summary, the results of the investigations conducted show that thehydrogenated condensed Palatinose prepared using the process of theinvention behaves similarly in the digestive tract to resistant starchor poorly degradable dietary fiber; that is, it is fermented only in thelarge intestine region, by the intestinal flora located there, with theformation of short-chain fatty acids. The fermentation products,particularly the resultant butyric acid, of hydrogenated condensedPalatinose, like the fermentation products of comparable, relativelyindigestible dietary fiber or resistant starch, lead to an intracellularincrease in the glutathione content and in the content of glutathioneS-transferase, which catalyzes glutathione reactions, the intracellularcontent of the two components being increased significantly incomparison to resistant starch.

One particularly preferred embodiment of the invention therefore relatesto the use of the hydrogenated condensed Palatinose of the invention asan agent or active substance for the treatment and/or prophylaxis ofdiseases which are associated with oxidative stress, especially for thetreatment and/or prophylaxis of cancer illnesses, particularly those ofthe large intestine region.

On the basis of the effects—known in the prior art and confirmed in thepresent invention—of the fermentation products of hydrogenated condensedPalatinose, in other words short-chain fatty acids, and particularlytheir inductive effects on the intracellular synthesis of theantioxidant glutathione and of glutathione S-transferase, theirantiproliferative effects on cancer cells, their antineoplastic effects,and their ability to increase cell differentiation, the hydrogenatedcondensed Palatinose product of this application is outstandinglysuitable for use as an agent for the treatment and/or prophylaxis of theaforementioned diseases.

In connection with the present invention a “disease” or “illness” isunderstood to refer to disruptions to the processes of life, and/orstates of deficiency, in an organism that are associated withsubjectively perceived and/or objectively determinable physical changes.“Oxidative stress” is a condition in which in the body or in specificorgans or tissues there is an imbalance between the formation and thebreakdown of free radicals, “free radicals” being molecules, or atomsand fragments thereof, that are characterized by a single impairedelectron and are therefore extremely reactive. By “diseases which areinduced by oxidative stress or are related to it” are meant, inaccordance with the invention, diseases such as cancer illnesses,particularly of the large intestine region, diabetes I and II,hypertension, stroke, male infertility, rheumatic illnesses, coronaryartery illnesses, acute myocardial infarction, and chronic inflammatorydiseases, particularly of the intestinal region. “Agents for treatingdiseases” are substances which in the body act directly as an activesubstance on cellular macromolecules and thereby induce a series offunctional changes, in other words bring about a biological effect, orwhose degradation products or fermentation products function in the bodyas active substances.

In a further preferred embodiment the present invention provides for theuse of the hydrogenated condensed Palatinose prepared in accordance withthe invention as an agent or active substance for strengthening theimmune defense against general infections.

Further embodiments envisage the use of the hydrogenated condensedPalatinose of the invention as an active substance for treating and/orpreventing constipation and as an active substance for reestablishingand maintaining a healthy microorganism flora in the digestive tract.

A further embodiment envisages the use of the hydrogenated condensedPalatinose of the invention as an active substance for improving theabsorption of food constituents, particularly of minerals such ascalcium, in the animal or human digestive tract, thereby preventingand/or reducing, in particular, phenomena of dietary deficiency.

Another embodiment of the invention provides for the use of thehydrogenated condensed Palatinose of the invention as an activesubstance for preventing and/or treating diarrhea illnesses,particularly those brought about by increased ion secretion and/ordeficient ion absorption (secretory diarrhea), which occurs in the caseof the majority of infections of the intestine with microorganisms(i.e., bacterial or viral enteritis), for example, the travel diarrheabrought about by enterotoxin-forming E. coli strains and also otherbacteria and parasites that are intestinal pathogens, and amebicdysentery.

The present invention further provides for the use of the condensedPalatinose of the invention as an active substance for the prophylaxisof infectious diseases, for the prophylaxis of intestinal illnesses, forthe prophylaxis of colon carcinogenesis, for the prophylaxis ofinflammatory illnesses and/or for the prophylaxis of osteoporosis.

In accordance with the invention it is envisaged in particular that thehydrogenated condensed Palatinose is administered in a dose sufficientto cure, or in particular to prevent, for example, the state of adisease caused by oxidative stress or the state of an infectiousdisease, to arrest the progress of such a disease and/or to alleviatethe symptoms. Preferably the hydrogenated condensed Palatinose of theinvention is administered orally, so that it can pass via thegastrointestinal tract into the large intestine. The dosage of thehydrogenated condensed Palatinose depends, among other factors, on theadministration form, on the age, sex, and body weight of the organism tobe treated, especially of the human being or animal to be treated, andon the severity of the illness.

In one preferred embodiment of the invention it is envisaged that thehydrogenated condensed Palatinose of the invention is administered inthe form of a pharmaceutical composition in order to treat, for example,diseases associated with oxidative stress, or infections, and/or toprevent said diseases or infections.

In connection with the present invention a “pharmaceutical composition”or a “drug” is a mixture used for diagnostic, therapeutic and/orprophylactic purposes, in other words to promote or reestablish thehealth of a human or animal body, which comprises at least one naturalor synthetically prepared active substance which produces thetherapeutic effect. The pharmaceutical composition may be either a solidor a liquid mixture. By way of example a pharmaceutical compositioncomprising the active substance may comprise one or morepharmaceutically acceptable excipients. Furthermore, the pharmaceuticalcomposition may comprise additives that are normally used in thetechnical field, such as stabilizers, manufacturing agents, releaseagents, disintegrants, lubricants, colorants, odorants, flavors,emulsifiers or other substances normally used for preparingpharmaceutical compositions.

In accordance with the invention it is envisaged in particular that thepharmaceutical composition comprising hydrogenated condensed Palatinosehas the form of a pharmaceutical composition for oral administration, inparticular the form of a suspension, tablet, pill, capsule, granules,powder or of a similarly suitable administration form. Although thehydrogenated condensed Palatinose used in accordance with the inventionis insensitive to gastric acid, the hydrogenated condensed Palatinosemay be included in drug forms which have a gastric-juice-resistant(enteric) coating. In such drug forms the active substances included inthe pharmaceutical composition are able to pass through the stomachunhindered and are preferentially released only in the upper or middlesections of the intestine. The composition of enteric coatings, andprocesses for producing such enteric coatings, are known in thetechnical field. In one particularly preferred embodiment of theinvention use is made of drug forms which have a retardedactive-substance release mechanism, in order thus to allow longer-termtherapy of diseases caused by oxidative stress. The construction and thecomposition of such drug forms with retarded active-substance releaseare likewise known in the technical field.

In a further particularly preferred embodiment of the invention it isenvisaged that the pharmaceutical composition comprising hydrogenatedcondensed Palatinose is used as part of a combination therapy for thetreatment, and in particular for the prophylaxis, of diseases caused,for example, by oxidative stress. In accordance with the invention,then, it is envisaged that, in addition to the active substancehydrogenated condensed Palatinose, at least one further active substanceand/or at least one further drug is administered at the same time forthe same indication. The combined use of hydrogenated condensedPalatinose and the at least one additional active substance or drug maybe aimed at intensifying therapeutic or prophylactic effects, but mayalso act on different biological systems in the organism and soreinforce the overall effect. Hydrogenated condensed Palatinose and theat least one additional drug may be administered either separately or inthe form of set combinations.

The selection of the additional drug or active substance dependsprimarily on the specific disease to be treated and on its severity.Where the illness, for example, is an illness associated with oxidativestress, such as a manifested colonic carcinoma, a basic chemotherapythat may be prescribed by the doctor, employing 5-fluorouracil, forexample, may be supported by simultaneous administration of hydrogenatedcondensed Palatinose. If the illness is manifested diabetes, then, forexample, the drug therapy of macroangiopathy in the diabetic, usingplatelet aggregation inhibitors, may be supported by simultaneousadministration of the hydrogenated condensed Palatinose of theinvention.

In a further preferred embodiment of the invention it is envisaged thatthe use of the hydrogenated condensed Palatinose for preventing and/ortreating diseases caused, for example, by oxidative stress, orinfections, is effected by administering the hydrogenated condensedPalatinose as an addition to animal feeds or to drinking water. Thehydrogenated condensed Palatinose thus passes along with the ingestedfood into the digestive tract of an animal, with subsequent fermentationby the flora in the large intestine region. Supplying the hydrogenatedcondensed Palatinose used in accordance with the invention by way of thefood is especially suitable for the prophylaxis of infectious diseasesor diseases caused, for example, by oxidative stress. Long-termprophylaxis of such illnesses is possible when animals are fed regularlywith feedstuffs comprising hydrogenated condensed Palatinose.

In connection with the present invention the term “feeds” or “animalfeedstuffs” means any substances or mixtures of substances that areintended to be fed, in unchanged, prepared, modified or processedcondition, to animals. Animal feeds may be in either solid or liquidform. The terms “feeds” and “animal feedstuffs” therefore also embracedrinking water for animals. The feeds may be either single feeds ormixed feeds. The active substances of the invention can be admixed tothe animal feed in either dissolved form or solid form. Foradministration to livestock such as pigs, the active substances of theinvention can be admixed in powder form, for example, to the mineralmixtures that are used for animal nutrition.

The hydrogenated condensed Palatinose used in accordance with theinvention may likewise be added, in accordance with the invention, tothe drinking water for animals. The addition of the hydrogenatedcondensed Palatinose to drinking water takes place preferablyimmediately prior to use, by adding the hydrogenated condensedPalatinose with drinking water, in the form for example of powders orgranules, so that the substances used in accordance with the inventioncan preferentially be dissolved rapidly.

In one further preferred embodiment of the invention it is envisagedthat the use of the hydrogenated condensed Palatinose for preventingand/or treating infections or diseases caused, for example, by oxidativestress is effected by using the hydrogenated condensed Palatinose as anaddition to foodstuffs, to dietetic foods or to drinking water intendedfor human consumption. The hydrogenated condensed Palatinose thereforepasses, together with the ingested food, into the digestive tract of thehuman being, with subsequent fermentation by the flora in the largeintestine region. Supplying the hydrogenated condensed Palatinose usedin accordance with the invention by way of the food is especiallysuitable for the prophylaxis of infectious diseases or diseases caused,for example, by oxidative stress. Long-term prophylaxis of suchillnesses is possible if foodstuffs comprising hydrogenated condensedPalatinose are consumed regularly.

In connection with the present invention foodstuffs are substances whichare intended to be consumed in unchanged, prepared or processed state byhumankind. Foodstuffs, in addition to their natural constituents, mayinclude further substances, which may be natural or synthetic in originand may have entered the foodstuff intentionally or unintentionally.Foodstuffs may be in either solid or liquid form. The term “foodstuff”therefore embraces all kinds of drinks, including drinking water, whichare intended for human consumption. The hydrogenated condensedPalatinose used in accordance with the invention may be admixed to thefoodstuff either in dissolved form or in the solid state.

In connection with the present invention “dietetic foods” are foodstuffswhich are intended to serve a particular nutritional purpose bysupplying particular nutrients or other substances which have anutrition-physiological effect, in a specific portion or in a specificform. Dietetic foods differ critically from foodstuffs of comparabletype in their composition or in their properties. Dietetic foods can beused in cases where it is necessary to meet particular nutritionalrequirements because of diseases, functional defects or allergicreactions to individual foodstuffs and/or ingredients thereof. Dieteticfoods may likewise be present in either solid or liquid form.

A further embodiment of the invention envisages the use of thehydrogenated condensed Palatinose of the invention as a pharmaceuticalcarrier in a pharmaceutical composition.

The present invention likewise provides for the use of the hydrogenatedcondensed Palatinose prepared in accordance with the invention forpreparing a pharmaceutical composition intended for the treatment and/orprophylaxis of diseases caused by oxidative stress.

Another preferred embodiment envisages the use of the hydrogenatedcondensed Palatinose of the invention for preparing a pharmaceuticalcomposition for strengthening the immune defense against generalinfections.

A preferred embodiment of the invention envisages the use of thehydrogenated condensed Palatinose of the invention as an addition tofoodstuffs and drinks that are intended for human consumption.

In one preferred embodiment of the invention it is therefore envisagedthat the hydrogenated condensed Palatinose prepared in accordance withthe invention is used as fiber, in particular as soluble fiber, in thefoodstuffs. In connection with the present invention “fiber” means afood constituent which is indigestible for human or animal enzymes butwhich is at least partly fermented by large intestine bacteria and henceto a small extent can be utilized for energy by the human or animalbody. “Soluble fiber” is soluble in solutions, especially aqueoussolutions. When used as fiber the hydrogenated condensed Palatinose ofthe invention regulates the energy density which results from thefraction of the main nutrients, and regulates the digestion process withregard to the transit time and to absorption in the small intestine. Thehydrogenated condensed Palatinose of the invention is a particularlysuitable soluble fiber on account of the fact that, owing to its verygood solubility in water, it is in dissolved form in the large intestineregion and consequently can be fermented completely or almost completelyby the intestinal flora. As compared with other forms of fiber that arefrequently used, such as wheat bran or oat bran, the hydrogenatedcondensed Palatinose of the invention, when used as fiber, has theadvantage, moreover, that it includes no substances which lead tounwanted side effects.

Another embodiment of the invention relates to the use of thehydrogenated condensed Palatinose of the invention as prebiotic fiber.Because of the fermentation of the hydrogenated condensed Palatinose ofthe invention to form short-chain fatty acids, particularly butyrate, inlarge amount, there is a marked reduction in pH in the large intestineregion, into the acidic range, when hydrogenated condensed Palatinose isused. Because of the reduced pH in the large intestine region, there isa deterioration in the living conditions for pathogenic intestinalmicroorganisms, and at the same time there is an improvement in theliving conditions for acidophilic microorganisms. The condensedPalatinose of the invention thus serves in particular, in accordancewith the invention, as a dietary fiber source.

In one preferred embodiment the hydrogenated condensed Palatinose of theinvention is used in combination with other soluble or insoluble,fermentable or nonfermentable forms of fiber. In one preferred versionof this embodiment the hydrogenated condensed Palatinose of theinvention is used in combination with at least one further form of fiberselected from the group of forms of fiber consisting of soluble fibersuch as short-chain fructo-oligosaccharides, long-chainfructo-oligosaccharides, galacto-oligosaccharides, hydrolyzed guar gum,such as “Sunfiber” or “Benefiber”, lactulose, xylo-oligosaccharides,lactosucrose, malto-oligosaccharides, such as “Fibersol-2” fromMatsutani, isomalto-oligosaccharides, gentio-oligosaccharides, glucosylsucrose, such as “Coupling Sugar” from Hayashibara, soybeanoligosaccharides, chito-oligosaccharides, chitosan oligosaccharides, andinsoluble fiber, such as resistant starch, oat fiber, wheat fiber,vegetable fiber, from peas or tomatoes, for example, fruit fiber, fromapples, berries and fruits of the carob tree, for example, such as“Caromax” from Nutrinova, celluloses and sugar beet fiber, such as“Fibrex” from Danisco.

Besides mixtures of the hydrogenated condensed Palatinose of theinvention with at least one of the aforementioned forms of fiber,preference is also given in accordance with the invention to mixtures ofthe hydrogenated condensed Palatinose of the invention, alone or inconjunction with at least one of the aforementioned forms of fiber, withcultures of probiotic lactobacteria, bifidobacteria, known as“synbiotics”. Depending on the use and form of administration, the addedprobiotic bifidobacteria cultures are in the form of live cultures or inthe form of dry cultures or long-life cultures.

The hydrogenated condensed Palatinose of the invention, alone or inconjunction with at least one of the aforementioned forms of fiberand/or with cultures of probiotic bifidobacteria, thus serves, inaccordance with the invention, as a dietary fiber source, for thetreatment and/or prevention of constipation, the reestablishment andmaintenance of a healthy microorganism flora in the digestive tract,improving the availability and the absorption of food constituents, suchas minerals, in the animal or human digestive tract in general forsupporting and reestablishing health, particularly for reconvalescence,and prevents, as set out above, the development of large intestinetumors and of inflammatory intestinal illnesses. With preference inaccordance with the invention the hydrogenated condensed Palatinose ofthe invention also serves for modulating and supporting the immunesystem of the human and animal body.

In another preferred embodiment the invention provides for the use ofthe hydrogenated condensed Palatinose of the invention for modulatingthe glycemic properties of foodstuffs or confectionery, especially forspecialty nutrition, infant nutrition or nutrition of persons havingdefects in glucose/insulin metabolism. By glycemic response is meant thechange in blood glucose level following intake of a readily digestiblecarbohydrate. The strongest glycemic response is occasioned by thosecarbohydrates of which, following oral intake, glucose can be rapidlyreleased and absorbed, by means of salivary, pancreatic orsmall-intestine enzymes. In the healthy organism a rise in blood glucoseproduces release of insulin, insulin stimulating the uptake of glucoseby peripheral tissue, skeletal muscles for example, so that the bloodlevel falls back to the base level. The hydrogenated condensedPalatinose of the invention is able to lower the glycemic index infoodstuffs of all kinds and can therefore be used for the prophylaxisand/or therapy of diabetes mellitus (type II) and other metabolicillnesses, preferably as a constituent of dietetic foodstuffs.

A further preferred embodiment of the invention envisages the use of thehydrogenated condensed Palatinose of the invention as a sweetener. Thehydrogenated condensed Palatinose of the invention possesses asweetening power of approximately 34% relative to sucrose (100%). Thehydrogenated condensed Palatinose of the invention can therefore be usednot only as soluble fiber, with the aforementioned positive propertiesassociated therewith, but also as a sugar replacer and/or sweetener,especially in dietetic products. Since the hydrogenated condensedPalatinose of the invention is not broken down by the human oral flora,it has advantageous acariogenic properties. Sweeteners comprisinghydrogenated condensed Palatinose are therefore advantageouslydistinguished by their acariogenicity. The invention accordingly alsoprovides a sweetener comprising the condensed Palatinose of theinvention.

A further preferred embodiment of the invention envisages the use of thehydrogenated condensed Palatinose of the invention for preparingfoodstuffs, confectionery, and animal feedstuffs. Envisaged inparticular is the use of the hydrogenated condensed Palatinose of theinvention for preparing acidic foodstuffs having a pH of 2 to 5,especially 2 to 4. Acidic foodstuffs of this kind support the prebioticeffect of the hydrogenated condensed Palatinose of the invention. Withparticular preference the hydrogenated condensed Palatinose of theinvention is used for preparing fruit juices or fruit-juicepreparations.

The present invention likewise provides foodstuffs of all kinds whichcomprise the hydrogenated condensed Palatinose of the invention alone orin conjunction with at least one further form of fiber and/or withcultures of probiotic Bifidobacteria. The invention envisages that theat least one further form of fiber is selected from the group of formsof fiber consisting of soluble fiber such as short-chainfructo-oligosaccharides, long-chain fructo-oligosaccharides,galacto-oligosaccharides, hydrolyzed guar gum, such as “Sunfiber” or“Benefiber”, lactulose, xylo-oligosaccharides, lactosucrose,malto-oligosaccharides, such as “Fibersol-2” from Matsutani,isomalto-oligosaccharides, gentio-oligosaccharides, glucosyl sucrose,such as “Coupling Sugar” from Hayashibara, soybean oligosaccharides,chito-oligosaccharides, chitosan oligosaccharides, and insoluble fiber,such as resistant starch, oat fiber, wheat fiber, vegetable fiber, frompeas or tomatoes, for example, fruit fiber, from apples, berries andfruits of the carob tree, for example, such as “Caromax” from Nutrinova,celluloses and sugar beet fiber, such as “Fibrex” from Danisco.

Since the hydrogenated condensed Palatinose of the invention is hardlycleaved under the pH conditions of the stomach and by the enzymes of thesmall intestine mucosa, the foodstuffs of the invention which comprisethe hydrogenated condensed Palatinose of the invention are,advantageously, reduced-calorie foodstuffs.

In a preferred embodiment of the invention the foodstuffs of theinvention are dairy products or milk products, examples being cheese,butter, yogurt, kefir, quark, sour milk, buttermilk, cream, condensedmilk, dry milk, whey, lactose, milk protein, milk mixture, half-fatmilk, whey mixture and milk fat products. In a further preferredembodiment of the invention the foodstuffs of the invention are bakeryproducts, particularly bread, including cookies, and fine bakeryproducts, including nonperishable bakery products. In furtherembodiments of the invention the foodstuffs of the invention are spreadsfor bread, margarine products and cooking fats, and also instantproducts and stock products. In other preferred embodiments of theinvention the foodstuffs of the invention are fruit products, especiallymarmalades, jams, jellies, fruit conserves, fruit pulp, fruit juices,fruit juice concentrates, fruit nectar and fruit powders. The foodstuffsof the invention comprising hydrogenated condensed Palatinose may inaccordance with the invention also be vegetable products, especiallyvegetable conserves, vegetable juices, and vegetable pulp. In furtherembodiments of the invention the foodstuffs comprising hydrogenatedcondensed Palatinose are nonalcoholic beverages, beverage basematerials, and beverage powders.

The present invention provides in a further preferred embodimentconfectionery comprising hydrogenated condensed Palatinose of theinvention. The hydrogenated condensed Palatinose of the inventionpossesses a sweetening power of approximately 34% in relation to sucrose(100%) and is therefore also used with particular advantage as a sugarreplacer and/or sweetener in confectioneries, particularly in dieteticproducts. The confectioneries of the invention are advantageouslydistinguished by their acariogenicity. The confectioneries of theinvention comprise, in particular, chocolate products, hard caramels,soft caramels, fondant products, jelly products, licorices, marshmallowproducts, desiccated coconut, coated chocolate candies, compressed candyproducts, candied fruits, cracknel, nougat products, ice confections,marzipan, chewing gum, muesli bars, and also ice cream or alcoholic ornonalcoholic sweet drinks.

A further preferred embodiment of the invention provides pharmaceuticalcompositions or drugs which comprise hydrogenated condensed Palatinoseof the invention as an active substance. In accordance with theinvention the drugs comprising hydrogenated condensed Palatinose can beused in particular for the treatment and/or prophylaxis of diseasesassociated with oxidative stress.

Further advantageous embodiments of the invention are apparent from thedependent claims.

The invention is illustrated with reference to the following examples.

EXAMPLE 1

Preparation of Condensed Palatinose

300 g of crystalline Palatinose were dissolved in a steel vessel,following the addition of 90 g of water, with stirring at 105° C. and,with subsequent addition of citric acid (0.02%, based on Palatinose),were concentrated under vacuum to a final temperature of 135° C. After135° C. had been reached this temperature was held for 30 minutes. Thiswas followed by cooling, and the reaction product was dissolved withfully deionized water. The resulting solution was purified by ionexchange on an H⁺-loaded cation exchanger and an OH⁻-loaded anionexchanger. Gel permeation chromatography was used in order to determinethe following composition: Range DP1 2% Range DP2 48%  Range DP4 28% Range DP6 12%  Range DP8 5% Range DP10 5%

The range DP2 corresponds substantially to isomaltulose.

The DP ranges were determined using Raftilose® L40 or Raftiline® St. ascontrol.

EXAMPLE 2

a) Hydrogenation of Condensed Palatinose

500 ml of the 30% strength reaction solution obtained in Example 1,containing 50% condensed Palatinose, 2% monosaccharides and 40%isomaltulose, were adjusted to a pH of 7.8 by adding 1 N NaOH, withstirring. Hydrogenation took place by means of a nickel catalyst (200 gmoist mass) in the presence of hydrogen (150 bar) at 70° C. withstirring.

Samples were taken after 0, 1, 2, 3 and 4 hours and tested for theirisomaltulose content and their 1,6-GPS and 1,1-GPM content. Thehydrogenation was ended following quantitative conversion of the freeisomaltulose to 1,1-GPM and 1,6-GPS.

Result: [hours] g/l 0 1 2 3 4 Isomaltulose 150.1 82.5 38.6 13.5 01,6-GPS 0 38.1 59.6 72.1 78.7 1,1-GPM 0 32.1 49.5 60.9 65.6 Total 150.1152.7 147.7 146.5 144.3

After a reaction time of 4 hours the isomaltulose contained in thecondensed Palatinose solution (see Example 1) had undergone completehydrogenation to 1,6-GPS and 1,1-GPM. The solution obtained after thecatalyst was separated off was purified by ion exchange on an H⁺-loadedcation exchanger and an OH⁻-loaded anion exchanger.

The total of isomaltulose, 1,6-GPS and 1,1-GPM showed virtually nochange during the reaction time; in other words, the amount of condensedsaccharides remained constant.

b) Isolation of Hydrogenated Condensed Palatinose

200 ml of a solution containing 15 of hydrogenated condensed Palatinosewere chromatographed by means of gel permeation chromatography(Fractogel HW40S, 3 separating columns each 120 cm long, 10 cm indiameter) at 55° C. with a flow rate of 600 ml/hour. The fractionscontaining the hydrogenated condensed Palatinose with a DP of 4-10 werecombined, concentrated and freeze-dried.

DP Distribution of the Hydrogenated Condensed Palatinose Isolated Rangearea % DP4 59 DP6 25 DP8 10 DP10 4 DP > 10 2

The lyophilizate obtained was characterized and used in in vitroanalyses for digestibility and fermentability with human feces.

EXAMPLE 3

Characterization of Hydrogenated Condensed Palatinose

Partial HCl hydrolysis of the hydrogenated condensed Palatinose productisolated in Example 2 was carried out as follows:

0.9 ml of a solution containing 1% hydrogenated condensed Palatinose wasmixed with 0.1 ml of 1 M HCl and then incubated at 47° C. for a maximumof 8 hours. Sampling took place after 0, 1, 2, 4, 6 and 8 hours. Theanalyses were carried out by means of HPAEC.

Result: [hours] mg/l 0 1 2 4 6 8 1,6-GPS 0 12.8 13.6 14.1 14.2 14.41,1-GPM 0 13.3 14.1 14.7 15.3 15.4 Isomaltulose 0 50.0 54.5 57.0 57.357.9 Total 0 76.1 82.2 85.5 86.8 87.7 Isomaltulose/ 0 2:1 2:1 2:1 2:12:1 1,6-GPS, 1,1-GPM ratio

The gentle hydrolysis resulted in controlled cleavage of the fructosidicbonds in the condensed Palatinose molecules without hydrolysis of theisomaltulose, 1,6-GPS and 1,1-GPM disaccharides.

All reducing ends in the condensed Palatinose molecules werehydrogenated to 1,6-GPS or 1,1-GPM.

The ratio between isomaltulose and the two 1,6-GPS and 1,1-GPMsubstances remained constant over the period of hydrolysis and amountedto 2:1.

EXAMPLE 4

Stability of the Hydrogenated Condensed Palatinose in Stomach and SmallIntestine

Stability in the Stomach

The stability of a substance on passage through the stomach can beascertained by determining the rate of hydrolysis at a pH of 2.0, usingsucrose and 1-kestose as controls.

For this purpose a solution containing 1% hydrogenated condensedPalatinose was incubated at a pH of 2.0 (0.01 M HCl) at 37° C. for 3hours. Samples were taken from the reaction mixture after 60, 120 and180 minutes. They were analyzed by means of HPAEC techniques.

Result:

Report as hydrolysis rates in % Incubation time Substance 0 min. 60 min.120 min. 180 min. Sucrose 0% 2% 5%  8% 1-Kestose 0% 11%  25%  36%Condensed 0% 4% 7% 10% Palatinose, hydrogenated

From the table it is apparent that hydrogenated condensed Palatinoseunderwent only limited cleavage under the pH conditions prevailing inthe stomach.

Stability to Pancreatic Enzymes

The pancreatic secretion contains a large number of hydrolases,including carbohydrate-cleaving enzymes which effect preferentialcleavage of α-1,4-glucans (starch, glycogen) to maltose andmalto-oligosaccharides.

The test of the stability of saccharides to pancreatic enzymes wascarried out as follows:

Solutions Required:

-   -   20 mM Na phosphate buffer, pH 7.0 plus 6 mM NaCl (solution 1)    -   1% strength starch solution (soluble starch according to        Zulkowski) in solution 1    -   1% strength condensed Palatinose solution, hydrogenated, in        solution 1    -   0.2% pancreatin (Sigma) dissolved in solution 1

Reaction Mixtures: Components Sample Control Saccharide solution 3.0 ml— Starch solution — 3.0 ml Enzyme solution 0.1 ml 0.1 ml

After 210 minutes of incubation in a thermal mixer (with shaking atintervals) at 37° C. the reaction was ended by heating at 95° C. for 15minutes. The samples were then analyzed by HPAEC. The sample containingstarch was fully hydrolyzed beforehand by heating in 1 M HCl at 95° C.for 3 hours.

Result: Substance Degradation rate (%) condensed Palatinose, <1hydrogenated soluble starch 85

It is evident that hydrogenated condensed Palatinose was not cleaved bythe pancreatic enzymes.

Cleavability by Small-Intestine α-Glucosidases

The enzyme complexes, saccharase/isomaltase and glucoamylase/maltase,situated in the mucosa of the small intestine ensure in vivo that thedisaccharides maltose and sucrose, and to some extentmalto-oligosaccharides as well, that enter the small intestine arecleaved to monosaccharides and as such are able to pass via theintestinal wall into the bloodstream.

The test of the stability of hydrogenated condensed Palatinose to theseenzymes was carried out as follows:

Enzyme Isolation:

The saccharase/isomaltase (SI) and glucoamylase/-maltase (GM) enzymecomplexes were isolated from porcine small intestine by the method of H.Heymann (Dissertation, Hannover, 1991).

The cleavability of the saccharide of the invention by small-intestineα-glucosidases was determined as follows:

Solutions Required:

-   -   triethanolamine (TRA) buffer, 0.1 M, pH 7.0    -   saccharide, 1% strength solution in TRA buffer    -   maltose or sucrose, as control substances, 1% strength in TRA        buffer    -   mucosa enzyme, dissolved in TRA buffer        Reaction Mixture:

1.2 ml of the carbohydrate solution, at a controlled temperature of 37°C., were admixed with 0.7 U of the saccharase/isomaltose orglucoamylase/maltase enzyme complex, respectively, at t=0. Mixing wasfollowed by incubation at 37° C. The reaction was stopped after 2 hoursby heating at 95° C. for 15 minutes. The monosaccharides formed and alsothe test substances used were assayed by HPAEC.

Result: Hydrolysis rate [%] Saccharide SI GM Sucrose 98 — Maltose 95 —Maltose — 96 condensed Palatinose, 7 1 hydrogenated

The results show that under the chosen conditions there was virtuallycomplete hydrolysis of sucrose or maltose in the case of the SI enzymecomplexes, and of maltose in the case of the GM enzyme complex, whilethe hydrogenated condensed Palatinose was cleaved only to a smallextent, or virtually not at all, by both enzyme complexes.

EXAMPLE 5

Metabolism of Hydrogenated Condensed Palatinose by Microorganisms (HumanFeces)

Incubating the carbohydrates with human feces allows conclusions to bedrawn on the rate of metabolism by the bacterial population and also onthe formation of butyrate, which is particularly important as asubstrate for colonocytes and is said to have a preventive function withregard to colonic carcinoma.

Besides hydrogenated condensed Palatinose, for comparison, Raftilose®P95 was used as a rapidly fermentable carbohydrate and resistant starchas a slowly fermentable carbohydrate.

The resistant starch used is Novelose 240 (National Starch), whoseresistant starch fraction was increased to 83% resistant starch byenzymatic treatment using α-amylase/amyloglucosidase and recovery of theinsoluble fraction.

In the case of the hydrogenated condensed Palatinose (Example 2)hydrogenated monosaccharides and disaccharides were separated by gelpermeation chromatography. This ensured that the mono-/disaccharidesalready completely or partially digested in the small intestine are nolonger available for metabolism and no longer falsify the result of thein vitro fermentation.

1. In Vitro Fermentation Medium

For the in vitro fermentation experiments the following medium was used:Tryptone 1.5 g Yeast extract 1.0 g KH₂PO₄ 0.24 g Na₂HPO₄ 0.24 g(NH₄)₂SO₄ 1.24 g NaCl 0.48 g MgSO₄ × 7 H₂O 0.10 g CaCl₂ × 2 H₂O 0.06 gFeSO₄ × 7 H₂O 2 mg Resazurin 1 mg Cysteine/HCl 0.5 ml Vitamin solution(according to DSM 141) 0.5 ml Trace element solution (according to DSM141) 9.0 ml NaHCO₃ 2.0 g H₂O, distilled add 1000 ml, pH 7.02. Cultivation of Intestinal Bacteria on the Test Oligosaccharides

9 ml of the anaerobic medium described above were admixed with 0.5%(w/v) of the test oligosaccharide and subsequently inoculated with 1 mlof a 10% feces suspension (mixed feces from two volunteers) in anaerobic50 mM phosphate buffer, pH 7.0, to which 0.5 g/l cysteine/HCl had beenadded as reducing agent. Hungate tubes were incubated with shaking at37° C. for 14-48 hours depending on oligosaccharide. Samples were takenat specific points in time and were analyzed for their residualoligosaccharide content, short-chain fatty acid content and lactic acidcontent, and for their pH.

Result:

% degradation rate for carbohydrates and butyrate content (mmol/l) afterin vitro fermentation: Butyrate content (final Hours sample) 7 14 22 28mmol/l Raftilose ® 100 — — — 2.5 P95 Resistant 15 37 66 89 11.8 starchCondensed 38 40 89 95 15.3 Palatinose, hydrogenated (>DP2)

The fructo-oligosaccharides (Raftilose® P95) were completely metabolizedafter just 7 hours. Following separation of the mono-/disaccharides,hydrogenated condensed Palatinose (Example 2) was fermented almostcompletely, at 98%, within 28 hours. The butyrate contents, at 12.8-17.8mmol/l, were of comparable order both for the resistant starch and forthe hydrogenated condensed Palatinose products. Only in the case of theRaftilose® P95 were significantly lower butyrate contents found.

EXAMPLE 6

Effect of Fermentation Supernatants on GST Activity and GlutathioneContent for the Colonic Cell Line HT29

The fermentation mixture obtained for the hydrogenated condensedPalatinose (see Example 5) was worked up as follows to prepare thefermentation supernatant:

1. Centrifugation of 10000×g for 20 minutes at 4° C., 2. sterilefiltration with 0.22 μm filter. The solution was stored at −18° C. untiluse.

The HT29 cells were preincubated for 48 hours. Then the fermentationsupernatants (10% by volume) or 10% by volume medium (control) wereadded. Subsequently the HAT 29 cells were incubated with thefermentation supernatants for a further 72 hours.

Prior to the determination of the glutathione S-transferase activity andthe glutathione content, the HAT 29 cells were treated as follows: thecells from the treated incubation batches (approx. 6×10⁶ cells/2.5 mlbatch) were suspended in an extraction buffer (20 mM Tris HCl, 250 mMsucrose, 1 mM dithiothreitol, 1 mM PMSF, 1 mM EDTA, pH 7.4) and treatedwith an Ultra-Turrax for 1 minute.

The total glutathione activity was determined by the method of Habig etal. (J. Biol. Chem. 249, 7130-39, 1974) with 1-chloro-2,4-dinitrobenzene(1 mM).

In the presence of glutathione (1 mM) the reaction took place at 30° C.and a pH 6.5. The conjugate formed was detected by spectrophotometry at340 nm and was used to calculate the activity. 1 μmol of conjugate perminute corresponds to one activity unit. Intracellular glutathione wasdetermined by means of a colorimetric test (glutathione assay kit,Calbiochem-Novabiochem).

Effect of Fermentation Supernatants of Hydrogenated Condensed Palatinoseon Constituents of the Colonic Carcinoma Cell Line HAT 29 GlutathioneS-transferases Fermentation (nmol/min × 10⁶ Glutathione supernatants ofcells (nmol/10⁶ cells) Hydrogenated condensed 68* 9.6* Palatinose (>DP2)Condensed Palatinose 45 6 (>DP2) Resistant starch 53 6 Control 40 6(without carbohydrate)*significant

The results say that in the case of the hydrogenated condensedPalatinose both the intracellular glutathione S-transferase activity andthe glutathione content are increased relative to the control, by 70%and 60% respectively. The unhydrogenated form of the condensedPalatinose, used for comparison, does not exhibit these significantincreases. The same applies to the resistant starch.

EXAMPLE 7

Determining the Sweetening Power of Hydrogenated Condensed Palatinose

To determine the sweetening power of hydrogenated condensed Palatinosethe hydrogenated condensed Palatinose is diluted with drinking water togive a solution with a strength of in each case 18%, 19%, 20%, 21%, 22%,23%, 24%, 25%, 26%, 27% and 28% and each solution is subsequently passedthrough a 0.45 μm membrane filter. As a standard for comparison an 8%strength aqueous sucrose solution is prepared.

At the first tasting the samples are handed over in the order indicatedabove. The testers, 9 persons, are to taste first the comparisonstandard and subsequently each one of the samples, and are to reportwhether the sugar standard or the sample is sweeter or whether they canfind any difference. Drinking water is used for neutralizing between thetastings.

On the basis of the results of the first tasting it is possible toreduce the number of samples to be tested for the second tasting. The27% to 20% strength aqueous hydrogenated condensed Palatinose solutionsare tasted by 8 testers, beginning with the highest concentration,against the comparison standard, under the conditions described above.

Calculation of Sweetening Power:

-   X_(l)=changeover point at which there is a change from “standard is    sweeter” to “no difference can be found in sweetening power” or from    “no difference can be found in sweetening power” to “standard is    sweeter”.-   X_(u)=changeover point at which there is a change from “no    difference can be found in sweetening power” to “sample is sweeter”    or from “sample is sweeter” to “no difference can be found in    sweetening power”.    ${{lower}\quad{threshold}\text{:}\quad L_{1}} = \frac{\Sigma\quad x_{1}}{N}$    ${{upper}\quad{threshold}\text{:}\quad L_{u}} = \frac{\Sigma\quad x_{u}}{N}$-   equivalent stimulus=(L_(u)+L_(l))/2-   uncertainty range=L_(u)−L_(l)    ${{sweetening}\quad{power}} = {{\frac{{sugar}\quad{concentration}}{{equivalent}\quad{stimulus}} \cdot 100}\%}$    Result:

As the result from two tastings the sweetening power of the hydrogenatedcondensed Palatinose of the invention was found to be approximately34%±2%.

APPLICATION EXAMPLE 1 Confectionery

Wine gums Recipe 1 2 3 4 5 6 7 Gelatin [kg] 10 14 11 0 0 20 15 Water[kg] 20 26 22 80 90 35 30 Sugar [kg] 40 35 35 40 50 40 40 Glucose syrup[kg] 10 10 40 15 10 40 20 Hydrogenated 25 40 55 20 45 40 20 condensedPalatinose [kg] Fruit acid [kg] 1.3 1.6 1.4 1.0 0.6 0.5 0.7 Glycerin[kg] 1.2 4 0 0 4.6 0 0 Gum arabic [kg] 0 0 0 80 84 0 0 Boilingtemperature 136 136 123 123 121 123 130 [° C.]

Soften or dissolve gelatin with water; boil sugar, glucose syrup andhydrogenated condensed Palatinose to the specified temperature, allow tocool a little; add gelatin, fruit acid and glycerin; cast composition,put in hot chamber, carry out powdering and oiling.

Dissolve gum arabic in water overnight and pass through a hairnet; boilsugar, glucose syrup and hydrogenated condensed Palatinose to thespecified temperature, allow to cool a little; add the gum solution,glycerin and fruit acid; cast composition, place in hot chamber, carryout powdering and oiling. Fruit jellies 25 kg sugar 25 kg hydrogenatedcondensed Palatinose 0.8 kg agar agar 30 kg water 11 kg apple pulp 0.5kg tartaric acid 0.06 kg flavor, essences or color

Soften agar in water, dissolve, add sugar and further ingredients, andboil to 105° C. Pour the composition into the corresponding molds. Hardcaramels Recipe 1 2 Hydrogenated condensed Palatinose [g] 3250 1500Sucrose [g] — 1500 Glucose syrup [g] — 1500 Water [g] 968.5 200 DL-malicacid [g] 30 30 Flavor [g] 6 6 Color [g] 3 3Recipe 1:

Hydrogenated condensed Palatinose and water are boiled to 160° C. andthen evacuated (−0.9 bar). After cooling to 120° C., the predissolvedDL-malic acid, flavor and color are stirred in. The melt is embossed orcast.

Recipe 2:

Sucrose, glucose syrup, hydrogenated condensed Palatinose and water areboiled to 135° C. and then evacuated. After cooling to 120° C., thepredissolved DL-malic acid, flavor and color are stirred in. The melt isembossed or cast. Soft caramels Recipe Hydrogenated condensed Palatinose[g] 164.50 Lycasin 80/55 [g] 325.00 Water [g] 32.50 Toffix P [g] 52.50Gelatin [g] 19.50 Monomuls 90-35 [g] 3.25 Lecithin [g] 1.30 Calciumcarbonate [g] 50.00 Acesulfame K [g] 0.33 Aspartame [g] 0.33 Flavor [g]1.3

Dissolve hydrogenated condensed Palatinose, Lycasin, sweetener andwater; at 120° C. stir in Toffix, lecithin and monomuls; at 125° C. stirin gelatin, calcium carbonate and flavor; carry out molding.

APPLICATION EXAMPLE 2 Dog Food

Dog biscuits 150 g quark 90 g milk 90 g edible oil 1 egg yolk 75 ghydrogenated condensed Palatinose 200 g dog flakes

Mix the ingredients, form small balls and bake at 200° C. for 20minutes. Cookies 150 g whole grain wheat flour 200 g whole grain oatflakes 30 g honey 50 g hydrogenated condensed Palatinose 5 g granulatedstock 100 g whole egg 150 g milk

Mix the ingredients, form balls and bake at 220° C. for 15 minutes.

APPLICATION EXAMPLE 3 Muesli

Muesli bars 200 g oat flakes 100 g cornflakes 100 g hazel nuts 50 gsunflower seeds 30 g desiccated coconut 75 g brown sugar 75 g honey 100g hydrogenated condensed Palatinose 50 g butter ½ lemon

Caramelize sugar, honey, hydrogenated condensed Palatinose, butter andthe juice of half a lemon. Mix oat flakes, corn flakes, nuts, sunflowerseeds and desiccated coconut and add. Thoroughly mix the composition andtip onto a baking sheet. Cut out bars and store under dry conditions.Wintertime fruit muesli 4 tbsp oat flakes 2 tbsp millet flakes 1 tbspwheatgerm flakes juice of 1 lemon 150 g yogurt 1 tbsp sea buckthorn 50 gchopped nuts 10 g raisins 400 g apples 200 g pears 300 g oranges 150 gbanana 80 g hydrogenated condensed Palatinose(tbsp = slightly heaped tablespoon)

Mix flakes, yogurt and sea buckthorn, add the nuts. Coarsely grate theapple and finely dice the other fruits, tip lemon juice over the appleand add hydrogenated condensed Palatinose. Summer muesli 150 g apricots,diced 150 g low-fat yogurt 40 g hydrogenated condensed Palatinose 30 gcornflakes

Breakfast cereals 69.3 g wheat flour type 405 15 g oat flour 1 g malt,light 2.1 g malt, dark 0.6 g salt 10 g water 12 g hydrogenated condensedPalatinose

Mix wheat flour, oat flour, light and dark malt, hydrogenated condensedPalatinose and salt. The water is added in an extruder. In the extruderthe dough is mixed, sheared, boiled, plastified and extruded throughannular dies. Subsequently the rings are dried and cooled.

APPLICATION EXAMPLE 4 Drinks

Power drink 3 oranges 2 tbsp wheat germ 35 g hydrogenated condensedPalatinose 200 g yogurt(tbsp = slightly heaped tablespoon)

Squeeze oranges, whisk with wheat germ and hydrogenated condensedPalatinose, and stir in yogurt. Hobbythek drink 150 ml orange juice 50ml mineral water 1 pinch HT multivitamin powder 1 tsp HT multimineralpowder 5 g HT apple-wheat fiber 7.5 g hydrogenated condensed Palatinose(tsp = slightly heaped teaspoon)

[Hobbythek is a German consumer affairs TV program which has given riseamong other things to certain “mix your own” ingredients for consumerproducts, labeled ‘HT’ in some of the recipes here] Driver 1 200 mlrosehip tea 100 ml grape juice 5 g HT apple-wheat fiber 1 tsp honey 5 ghydrogenated condensed Palatinose(tsp = slightly heaped teaspoon)

Driver 2 300 ml rosehip tea 5 g HT apple-wheat fiber 1 tbsp quark 100 mlgrape juice 10 g hydrogenated condensed Palatinose(tbsp = slightly heaped tablespoon)

Aronia-apple fiber drink 200 ml mineral water 1½ tsp aronia fruit syrup1 tsp apple fruit syrup 2 tsp HT apple fiber 10 g hydrogenated condensedPalatinose(tsp = slightly heaped teaspoon)

Sportspersons' cocktail 2 tomatoes ½ cucumber 250 g carrots 250 g apples4 tbsp cream parsley 50 g hydrogenated condensed Palatinose(tbsp = slightly heaped tablespoon)

Juice tomatoes, cucumber, carrots and apples, and add cream, parsley andcondensed Palatinose. Tomato cocktail 6 tomatoes 4 tbsp cream juice of 1orange 1 pinch salt 7.5 g hydrogenated condensed Palatinose 1 pinchpaprika 2 squirts Tabasco(tbsp = approx. 12 ml)

Puree tomatoes and stir together with remaining ingredients. Orangenectar containing 50% fruit: 120 kg orange nectar base 50:11; juicecontent 400%; extract content 50% 48 kg sugar syrup 65% solids 60 kghydrogenated condensed Palatinose 820 kg drinking water

Lemonade 4.5 kg lemonade base 3:100; extract content 40% 60 kg sugarsyrup 65% solids 75 kg hydrogenated condensed Palatinose 888.5 kgdrinking water 8 kg CO₂

Application Example 5: Fruit preparations Red fruit jelly 330 g sourcherries 150 g blueberries 300 g raspberries 300 g strawberries 60 gstarch 1 l fruit juice 60 g sugar 50 g hydrogenated condensed Palatinose

Stir up the starch with a little cold fruit juice and stir into theboiling fruit juice. Leave to boil for 5 minutes. Add the fruits, thesugar and the hydrogenated condensed Palatinose. Cold rhubarb soup 750 grhubarb ½ l water juice of ½ lemon 120 g sugar 75 g hydrogenatedcondensed Palatinose 0.2 l white wine

Wash rhubarb, cut, steam with water and the lemon juice until soft.While still warm, stir together with sugar and hydrogenated condensedPalatinose, leave to cool, and stir in white wine. Fruit puree 750 gfruits 30 g fruit juice 50 g hydrogenated condensed Palatinose 3 ml rum

Puree the ingredients in a mixer. Strawberry cream 375 g strawberries 50g hydrogenated condensed Palatinose 1 small pack vanilla sugar 2 sheetsgelatin white 2 sheets gelatin red 250 ml cream

Puree berries, add hydrogenated condensed Palatinose and vanilla sugar,add dissolved gelatin, and cool. Whip the cream until stiff and fold in.Apricot cream 100 g apricots 375 ml water 30 g sugar 50 g hydrogenatedcondensed Palatinose 1 pack vanilla sugar 4 sheets white gelatin 1 sheetred gelatin 250 ml cream

Boil apricots, water, sugar, hydrogenated condensed Palatinose andvanilla sugar for 30 minutes. Dissolve gelatin in apricot compote, pureecomposition, and cool. Beat cream until stiff and fold in.

APPLICATION EXAMPLE 6 Yogurt

Lemon yogurt shake 600 g low fat yogurt juice of 4 lemons 4 tsp honey 30g hydrogenated condensed Palatinose 4 egg yolks

Mix ingredients. Lemon yogurt cream 4 eggs 40 g sugar 40 g hydrogenatedcondensed Palatinose 25 ml lemon juice 300 g yogurt 6 g gelatin powder

Soften the gelatin. Separate yolks from whites. Mix yogurt, yolk, sugar,hydrogenated condensed Palatinose and lemon juice. Dissolve the gelatinand add. Beat the egg white to a foam and fold in.

APPLICATION EXAMPLE 7 Jams

Südzucker preserving sugar recipes PS 1 PS 1 plus 1 Recipe plus 1fructose Pectin [g] 7.370 7.370 Citric acid [g] 10.700 10.700Hydrogenated condensed 490.965 490.965 Palatinose [g] Sugar [g] 490.9650.000 Fructose [g] 0.000 490.965 Fruit [g] 970.000 970.000 PS 2 PS 3Recipe plus 1 PSwS plus 1 Amidated pectin [g] 6.41 8.00 11.55 Citricacid [g] 3.80 3.80 3.80 Sorbic acid [g] 0.63 0.63 0.63 Hydrogenatedcondensed 489.17 110.00 484.02 Palatinose [g] Sugar [g] 0.00 377.57 0.00Fruit [g] 970.00 1000.00 1455.00Boiling time 4 minutes in each case (except for PSwS)PSwS: boiling time 5 minutes

Sour cherry jam with amaretto and vanilla 1 kg sour cherries 3 vanillapods 500 g preserving sugar 2:1 40 ml amaretto (almond liqueur)

Thoroughly comminute half of the sour cherries in a mixer. Mix thepureed fruit with the remainder of the cherries, the pulp of the vanillapods and the preserving sugar, and bring to the boil with stirring.Leave to bubble at the boil for 4 minutes. Add the amaretto. Introducethe jam into glass jars while still hot, and seal immediately. Rhubarband strawberry jam 750 g rhubarb 250 g strawberries 1000 g preservingsugar 1:1 3 small packs vanilla sugar 1 tbsp finely chopped lemon balm

Cut rhubarb and strawberries into pieces. Mix the fruits with preservingsugar and vanilla sugar and leave covered for 3 to 4 hours to steep. Thebring to the boil with stirring and boil at the bubble for 4 minutes.Stir in the lemon balm. Introduce the jam into glass jars while stillhot, and seal immediately. Pumpkin jelly 1.5 kg pumpkin 1.2 l water 1 kgpreserving sugar 1:1 juice of 2 lemons 1 tsp chopped mint

Cut the pumpkin into cubes and boil with the water for 20 to 30 minutesuntil soft. Pass the juice through a cloth. Mix 750 ml of cold juicewith preserving sugar and lemon juice and bring to the boil withstirring. Leave boiling at the bubble for 4 minutes. Stir in the mint.Introduce the jelly into glass jars while still hot, and sealimmediately. Strawberry jam with Grand Marnier 1 kg strawberries 1 kgpreserving sugar 1 untreated orange 65 g Grand Marnier (orange liqueur)

Crush the strawberries, add preserving sugar and the grated peel of theorange, and mix all ingredients thoroughly. Bring to the boil withstirring and leave stirring at the bubble for 4 minutes. Stir in GrandMarnier. Introduce into glass jars while still hot, and sealimmediately.

APPLICATION EXAMPLE 8 Bakery Products

Yeast is used as raising agent in the recipes listed. The capacity ofbaker's yeast to use the hydrogenated condensed Palatinose of theinvention as a substrate is limited. Therefore only some of the sugar isreplaced by hydrogenated condensed Palatinose. Croissant Component Yeast[g] 25 Cream [g] 250 Sugar [g] 25 Hydrogenated condensed Palatinose [g]35 Wheat flour type 550 [g] 400 Salt [g] 0.15 Margarine [g] 200 Egg yolk[g] 50

Stir together yeast, lukewarm cream, 1 pinch of salt and 1 pinch offlour. Leave to prove for 10 minutes. Knead with other ingredients andleave to prove for 20 minutes. Knead dough thoroughly, roll out, cut out15 triangles and roll up to croissants. Leave to rise briefly and bakeat 200° C. for 10 minutes. White bread Component Yeast [g] 40 Sugar [g]15 Hydrogenated condensed Palatinose [g] 20 Wheat flour type 550 [g]1000 Milk [g] 500 Margarine [g] 250 Grated lemon rind [g] 2.5 Whole egg[g] 50

Stir yeast with sugar into lukewarm milk and leave to prove for 10minutes. Knead with the other ingredients and leave to prove for 20minutes. Bake in a loaf tin at 175° C. for 45 minutes. Sesame breadComponent Yeast [g] 60 Milk [g] 500 Sugar [g] 30 Hydrogenated condensedPalatinose [g] 45 Wheat flour type 550 [g] 300 Rye flour type 1150 [g]250 Wheat meal type 1700 [g] 200 Salt [g] 0.15 Margarine [g] 100 Sesameseed [g] 100

For preparation see White bread Basic recipe for short pastry Shortpastry without Component Short pastry sugar Flour [g] 250 250 Sugar [g]35 0 Hydrogenated condensed Palatinose [g] 45 90 Salt [g] 0.15 0.15Chilled margarine [g] 125 125 Whole egg [g] 50 50

Briefly mix all ingredients with kneading hook at lowest setting andthen knead thoroughly at a higher setting. Chill dough before baking.Basic recipe for sponge mixture Sponge mixture Sponge without Componentmixture sugar Margarine [g] 125 125 Sugar [g] 65 0 Hydrogenatedcondensed Palatinose [g] 90 180 Salt [g] 0.15 0.15 Whole egg [g] 100 100Flour [g] 250 250 Baking powder [g] 8 8 Milk [g] 125 125

Stir all ingredients with the whisk first on a low setting, then at thehighest setting. The two sponge mixtures thus prepared go browner than asponge mixture with sugar, and are less sweet. It is thereforerecommended that the two sponge mixtures set out above be sweetened witha sweetener if required. Basic fatless sponge recipe Fatless spongeFatless without Component mixture sugar Whole egg [g] 200 200 Water [g]60 60 Sugar [g] 65 0 hydrogenated condensed Palatinose [g] 90 180 Flour[g] 75 75 Corn starch [g] 75 75 Baking powder 0.5 0.5

Beat egg yolk, water, sugar, hydrogenated condensed Palatinose and saltto a foam with the whisk. Add very stiffly beaten egg white to the eggyolk mixture. Mix flour, corn starch and baking powder, sieve onto thefoamy mixture, and fold in carefully.

1. A process for preparing hydrogenated condensed Palatinose, comprisingthe catalytic hydrogenation of a solution comprising condensedPalatinose.
 2. The process of claim 1, wherein the condensed Palatinoseis obtained by heat-treating an aqueous Palatinose solution having a pHof 3 to 6 at a temperature of 100° C. to 170° C. under atmosphericpressure or reduced pressure.
 3. The process of claim 2, wherein theaqueous Palatinose solution to be condensed is prepared by dissolvingPalatinose in water.
 4. The process of claim 2, wherein acidic catalystsare added to the aqueous Palatinose solution.
 5. The process of claim 4,wherein the acidic catalysts are selected from the group consisting ofH⁺-loaded, strongly acidic cation exchangers, organic acids, boric acid,and a combination of phosphoric acid with potassium dihydrogen phosphateor ammonium sulfate.
 6. The process of claim 5, wherein the organicacids are selected from the group consisting of citric acid, malic acid,succinic acid and tartaric acid.
 7. The process of claim 2, wherein thecondensed Palatinose is obtained by heat-treating an aqueous Palatinosesolution in the presence of 0.02% by weight citric acid, based onPalatinose, in vacuo at a temperature of 135° C.
 8. The process of claim7, wherein the condensed Palatinose comprises about 48% uncondensedPalatinose, about 28% Palatinose dimers, about 12% Palatinose trimers,about 5% Palatinose tetramers, about 5% Palatinose pentamers, and about2% hydrolysis products.
 9. The process of claim 1, comprisinghydrogenating condensed Palatinose obtained by reacting Palatinose withanhydrous hydrofluoric acid at a temperature of 0° C. to 20° C.
 10. Theprocess of claim 9, wherein the condensed Palatinose comprises about 73%to 94% Palatinose dimers.
 11. The process of claim 1, comprisinghydrogenating condensed Palatinose obtained from a Palatinose melt byadding Palatinose to a solution of a catalytically active, acidicsubstance in water to form a mixture and heating the mixture at atemperature of 130° C. to 160° C.
 12. The process of claim 11, whereinthe mixture comprises 4% to 12% by weight water and 0.05% to 0.5% byweight acidic substance.
 13. The process of claim 11, wherein the acidicsubstance is selected from the group consisting of an H⁺-loaded,strongly acidic cation exchanger, an organic acid, boric acid, and acombination of phosphoric acid with potassium dihydrogen phosphate orammonium sulfate.
 14. The process of claim 13, wherein the organic acidis citric acid.
 15. The process of claim 11, wherein the condensedPalatinose comprises 15% to 45% by weight uncondensed Palatinose, 35% to60% by weight Palatinose dimers, less than 10% by weight Palatinosetrimers, and less than 5% by weight Palatinose tetramers and Palatinosepentamers.
 16. The process of claim 15, wherein the fraction ofuncondensed Palatinose in the condensed Palatinose is reduced bydepletion.
 17. The process of claim 16, wherein the uncondensedPalatinose is depleted by chromatographic separation of the uncondensedPalatinose from condensed Palatinose.
 18. The process of claim 1,wherein the catalytic hydrogenation of the solution comprising condensedPalatinose takes place at elevated temperature under elevated pressurein the presence of hydrogen and using a catalyst.
 19. The process ofclaim 18, wherein the solution comprising condensed Palatinose isadjusted to a pH of 6 to 8 prior to hydrogenation.
 20. The process ofclaim 19, wherein the pH of the solution comprising condensed Palatinoseis adjusted to 7.8 by adding aqueous sodium hydroxide solution.
 21. Theprocess of claim 18, wherein the hydrogenation takes place at atemperature of 40° C. to 140° C.
 22. The process of claim 21, whereinthe hydrogenation takes place at a temperature of 60° C. to 80° C. 23.The process of claim 22, wherein the hydrogenation takes place at atemperature of 70° C.
 24. The process of claim 18, wherein thehydrogenation takes place at a pressure of 50 to 230 bar.
 25. Theprocess of claim 24, wherein the pressure is 100 to 200 bar.
 26. Theprocess of claim 25, wherein the pressure is 150 bar.
 27. The process ofclaim 18, wherein the catalyst comprises a mixture of a pure Raney metaland a Raney metal alloy.
 28. The process of claim 27, wherein the Raneymetal is nickel, copper, cobalt or iron.
 29. The process of claim 27,wherein the Raney metal alloy is an alloy of nickel, copper, cobalt oriron with a material selected from the group consisting of aluminum, tinand silicon.
 30. The process of claim 18, wherein the catalyst comprisesas an active component one or more metals from transition group VIII ofthe periodic table on a support.
 31. The process of claim 30, whereinthe active component comprises at least one of ruthenium, palladium andrhodium.
 32. The process of claim 30, wherein the catalyst supportcomprises at least one of activated carbon, aluminum oxide, zirconiumoxide and titanium dioxide.
 33. The process of claim 18, wherein thehydrogenation takes place with stirring.
 34. The process of claim 18,wherein the hydrogenation takes place over a period of at least 2 to 5hours.
 35. The process of claim 34, wherein the hydrogenation takesplace over a period of at least 4 hours.
 36. The process of claim 18,wherein the hydrogenation takes place continuously, semibatchwise orbatchwise.
 37. The process of claim 18, wherein the hydrogenation iscarried out in a fixed-bed process or a suspension process.
 38. Theprocess of claim 1, wherein, following hydrogenation of the solutioncomprising condensed Palatinose, a product mixture is obtained thatcomprises 25% to 36% by weight hydrogenated condensed Palatinose havinga DP of 4, 9% to 15% by weight hydrogenated condensed Palatinose havinga DP of 6, 3% to 7% by weight hydrogenated condensed Palatinose having aDP of 8, 3% to 7% by weight hydrogenated condensed Palatinose having aDP of 10, 3% to 7% by weight unhydrogenated condensed Palatinose, and40% to 55% by weight hydrogenated uncondensed Palatinose.
 39. Theprocess of claim 1, wherein, following hydrogenation, hydrogenatedcondensed Palatinose having a DP of 4 to 10 is separated from thereaction mixture.
 40. The process of claim 39, wherein said hydrogenatedcondensed Palatinose having a DP of 4 to 10 is separated from thereaction mixture by chromatography.
 41. The process of claim 39, whereinthe hydrogenated condensed Palatinose, following separation from thereaction mixture, comprises 30% to 55% by weight hydrogenated condensedPalatinose having a DP of 4, 20% to 30% by weight hydrogenated condensedPalatinose having a DP of 6, 7% to 13% by weight hydrogenated condensedPalatinose having a DP of 8, and 2% to 6% by weight hydrogenatedcondensed Palatinose having a DP of
 10. 42. A hydrogenated condensedPalatinose obtained by hydrogenating condensed Palatinose according tothe process of claim 1, said hydrogenated condensed Palatinosecomprising at least hydrogenated condensed Palatinose having a DP of 4,hydrogenated condensed Palatinose having a DP of 6, hydrogenatedcondensed Palatinose having a DP of 8, and hydrogenated condensedPalatinose having a DP of
 10. 43. The hydrogenated condensed Palatinoseof claim 42, comprising at least one compound of the formula (1)

obtained from α-2→1-linked di-Palatinose, for n=0 (DP 4):O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitolandO-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]-D-mannitol;at least one compound of the formula (2)

obtained from β-2→1-linked di-Palatinose for n=0 (DP 4):O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitolandO-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→1)-O-[α-D-glucopyranosyl-(1→6)]-D-mannitol;at least one compound of the formula (3)

obtained from α-2→3-linked di-Palatinose:O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitolandO-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol;at least one compound of the formula (4)

obtained from α-2→4-linked di-Palatinose:O-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitolandO-α-D-glucopyranosyl-(1→6)-α-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol;at least one compound of the formula (5)

obtained from β-2→3-linked di-Palatinose:O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitolandO-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol;and and at least one compound of the formula (6)

obtained from β-2→4-linked di-Palatinose:O-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→4)-O-[α-D-glucopyranosyl-(1→6)]-D-sorbitolandO-α-D-glucopyranosyl-(1→6)-β-D-fructofuranosyl-(2→3)-O-[α-D-glucopyranosyl-(1→1)]-D-mannitol.44. The hydrogenated condensed Palatinose of claim 42, wherein thefraction of hydrogenated condensed Palatinose having a DP of 4 is 30% to55% by weight, the fraction of hydrogenated condensed Palatinose havinga DP of 6 is 20% to 30% by weight, the fraction of hydrogenatedcondensed Palatinose having a DP of 8 is 7% to 13% by weight, and thefraction of hydrogenated condensed Palatinose having a DP of 10 is 2% to6% by weight.
 45. The hydrogenated condensed Palatinose of claim 42,wherein the fraction of hydrogenated condensed Palatinose having a DP of4 is 35% to 50% by weight.
 46. The hydrogenated condensed Palatinose ofclaim 42, wherein the fraction of hydrogenated condensed Palatinosehaving a DP of 6 is 22% to 28% by weight.
 47. The hydrogenated condensedPalatinose of claim 42, wherein the fraction of hydrogenated condensedPalatinose having a DP of 8 is 8% to 12% by weight.
 48. The hydrogenatedcondensed Palatinose of claim 42, wherein the fraction of hydrogenatedcondensed Palatinose having a DP of 10 is 3% to 5% by weight.
 49. Thehydrogenated condensed Palatinose of claim 42, further comprising 6% to12% by weight unhydrogenated condensed Palatinose having a DP of
 4. 50.The hydrogenated condensed Palatinose of claim 42, which is at leastsubstantially resistant to breakdown in at least one of a mammalianstomach and a mammalian digestive tract.
 51. (canceled)
 52. (canceled)53. (canceled)
 54. (canceled)
 55. (canceled)
 56. (canceled) 57.(canceled)
 58. (canceled)
 59. (canceled)
 60. (canceled)
 61. (canceled)62. (canceled)
 63. (canceled)
 64. (canceled)
 65. (canceled)
 66. Acomposition comprising the hydrogenated condensed Palatinose of claim 42and cultures of Bifidobacteria.
 67. A composition comprising thehydrogenated condensed Palatinose of claim 42 and at least one furtherform of fiber selected from the group consisting of short-chainfructo-oligosaccharides, long-chain fructo-oligosaccharides,galacto-oligosaccharides, hydrolyzed guar gum, lactulose,xylo-oligosaccharides, lactosucrose, malto-oligosaccharides,isomalto-oligosaccharides, gentio-oligosaccharides, glucosyl sucrose,soybean oligosaccharides, chito-oligosaccharides, chitosanoligosaccharides, resistant starch, oat fiber, wheat fiber, vegetablefiber, fruit fiber, celluloses, and sugar beet fiber.
 68. A foodstuffcomprising the hydrogenated condensed Palatinose of claim
 42. 69. Thefoodstuff of claim 68, wherein the foodstuff is selected from the groupconsisting of dairy products and milk products.
 70. The foodstuff ofclaim 69, wherein said dairy products and milk products are selectedfrom the group consisting of cheese, butter, yogurt, kefir, quark, sourmilk, buttermilk, cream, condensed milk, dry milk, whey, lactose, milkprotein, milk mixture, half-fat milk, whey mixture, and milk fatproducts.
 71. The foodstuff of claim 68, wherein the food stuffcomprises bakery products.
 72. The foodstuff of claim 71, wherein saidbakery products are selected from the group consisting of bread,including cookies, and fine bakery products, including nonperishablebakery products.
 73. The foodstuff of claim 68, wherein the foodstuffcomprises a spread for bread.
 74. The foodstuff of claim 68, wherein thefoodstuff comprises at least one of margarine products and cooking fats.75. The foodstuff of claim 68, wherein the foodstuff comprises at leastone of instant products and stock products.
 76. The foodstuff of claim68, wherein the foodstuff comprises a fruit product.
 77. The foodstuffof claim 76, wherein the foodstuff comprises at least one of marmalades,jams, jellies, fruit conserves, fruit pulps, fruit juices, fruit juiceconcentrates, fruit nectar, and fruit powders.
 78. The foodstuff ofclaim 68, wherein the foodstuff comprises a vegetable product.
 79. Thefoodstuff of claim 78, wherein the foodstuff comprises at least one ofvegetable conserves, vegetable juices, and vegetable pulp.
 80. Thefoodstuff of claim 68, wherein the foodstuff comprises a spice mixture.81. The foodstuff of claim 68, wherein the foodstuff comprises at leastone of nonalcoholic beverages, beverage base materials, and beveragepowders.
 82. The foodstuff of claim 68, which is a reduced-caloriefoodstuff.
 83. A confectionery product comprising the hydrogenatedcondensed Palatinose of claim
 42. 84. The confectionery product of claim83, wherein said product is selected from the group consisting ofchocolate, hard caramels, soft caramels, fondant products, jellyproducts, licorices, marshmallow products, desiccated coconut, coatedchocolate candies, compressed candy products, candied fruits, cracknel,nougat products, ice confections, marzipan, chewing gum, muesli bars,ice cream and alcoholic and nonalcoholic sweet drinks.
 85. Theconfectionery product of claim 83, wherein said product comprises areduced-calorie confectionery product.
 86. A dietetic specialty foodparticularly useful for the nutrition of persons having glucoseintolerance, comprising hydrogenated condensed Palatinose of claim 42.87. An infant food, comprising the hydrogenated condensed Palatinose ofclaim
 42. 88. A sweetener comprising the hydrogenated condensedPalatinose of claim
 42. 89. A pharmaceutical composition comprising thehydrogenated condensed Palatinose of claim
 42. 90. The pharmaceuticalcomposition of claim 89, comprising hydrogenated condensed Palatinose asan active substance.
 91. The pharmaceutical composition of claim 89,comprising hydrogenated condensed Palatinose as a pharmaceuticalcarrier.
 92. A method for preventing or treating a disease caused due tooxidative stress, said method comprising administering to a subject inneed thereof a therapeutically effective amount of the hydrogenatedcondensed Palatinose of claim
 42. 93. The method of claim 92, whereinthe disease is selected from the group consisting of cancer, diabetes Iand II, hypertension, stroke, male infertility, rheumatic illnesses,coronary artery illnesses, acute myocardial infarction and chronicinflammatory diseases.
 94. A method for strengthening the immune systemof a subject against infection, said method comprising administering toa subject in need of such strengthening a therapeutically effectiveamount of the hydrogenated condensed Palatinose of claim
 42. 95. Themethod of claim 92, wherein the hydrogenated condensed Palatinose isadministered in the form of a pharmaceutical composition.
 96. The methodof claim 95, wherein said pharmaceutical composition is in a formselected from the group consisting of a suspension, a syrup, a tablet, apill, a capsule, granules and a powder.
 97. The method of claim 94,wherein the hydrogenated condensed Palatinose is administered in theform of a pharmaceutical composition.
 98. The method of claim 97,wherein said pharmaceutical composition is in a form selected from thegroup consisting of a suspension, a syrup, a tablet, a pill, a capsule,granules, and a powder.
 99. A method for forming a pharmaceuticalcarrier for a pharmaceutical composition, wherein the method comprisesincluding in said pharmaceutical carrier an effective amount of thehydrogenated condensed Palatinose of claim
 42. 100. A method for forminga pharmaceutical composition for preventing or treating a disease causedby oxidative stress, wherein the method comprising incorporating intothe pharmaceutical composition a sufficient amount of the hydrogenatedcondensed Palatinose of claim 42 to prevent or treat said disease in asubject in need thereof.
 101. A method for forming a pharmaceuticalcomposition for strengthening the immune system of a subject againstinfection, wherein the method comprises incorporating into thepharmaceutical composition a sufficient amount of the hydrogenatedcondensed Palatinose of claim 42 to strengthen the immune system of asubject in need thereof.
 102. A method for preparing a foodstuff or adrink intended for human consumption which comprises adding to thefoodstuff or drink an amount of the hydrogenated condensed Palatinose ofclaim 42 effective to produce a desired result.
 103. The method of claim102, wherein said hydrogenated condensed Palatinose is added to thefoodstuff or drink as a soluble fiber.
 104. The method of claim 103,wherein said fiber is a prebiotic fiber.
 105. A method for modulatingthe glycemic properties of foodstuffs or confectionery products, whereinthe method comprises adding to the foodstuff or confectionery product anamount of the hydrogenated condensed Palatinose of claim 42 effective tomodulate the glycemic properties thereof.
 106. A method for producing asweetening composition which comprises incorporating into thecomposition an effective amount of the hydrogenated condensed Palatinoseof claim
 42. 107. A method for preparing a foodstuff or a confectionery,which comprises incorporating into the foodstuff or confectionery thehydrogenated condensed Palatinose of claim
 42. 108. The method of claim107, wherein the foodstuff is an acidic foodstuff having a pH of 2 to 5.109. The method of claim 108 wherein the pH is 2 to
 4. 110. A method forpreparing fruit juice or a fruit preparation which comprisesincorporating into the juice or preparation the hydrogenated condensedPalatinose of claim 42.